# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2015

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

data_Agphenyl
_database_code_depnum_ccdc_archive 'CCDC 1413568'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H23 Ag Cl N7 O6'
_chemical_formula_weight         564.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/m'

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

_cell_length_a                   21.2466(16)
_cell_length_b                   7.9440(6)
_cell_length_c                   15.8517(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.6690(10)
_cell_angle_gamma                90.00
_cell_volume                     2200.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1144
_exptl_absorpt_coefficient_mu    1.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS Smart APEX II'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10334
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         24.70
_reflns_number_total             2014
_reflns_number_gt                1935
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0167P)²+4.5821P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2014
_refine_ls_number_parameters     178
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0179
_refine_ls_wR_factor_ref         0.0445
_refine_ls_wR_factor_gt          0.0442
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.0000 0.25258(2) 0.0000 0.01498(7) Uani 1 2 d S . .
Cl1 Cl 0.12332(3) 0.5000 0.41909(4) 0.01613(13) Uani 1 2 d S . .
N2 N 0.04033(11) 0.0000 0.27538(15) 0.0134(4) Uani 1 2 d S . .
C6 C -0.01835(13) 0.0000 0.37195(17) 0.0132(5) Uani 1 2 d S . .
O2 O 0.16285(8) 0.35162(18) 0.42136(12) 0.0334(4) Uani 1 1 d . . .
N4 N 0.20461(11) 0.5000 0.26418(15) 0.0158(4) Uani 1 2 d S . .
O3 O 0.04730(11) 0.5000 0.32593(15) 0.0286(5) Uani 1 2 d S . .
N3 N 0.10365(8) 0.41254(19) 0.11835(11) 0.0161(3) Uani 1 1 d . . .
N1 N 0.00877(8) 0.08740(19) 0.12538(10) 0.0149(3) Uani 1 1 d . . .
C2 C 0.16472(10) 0.3646(2) 0.20691(13) 0.0169(4) Uani 1 1 d . . .
H2 H 0.1785 0.2533 0.2273 0.020 Uiso 1 1 calc R . .
C3 C 0.27717(14) 0.5000 0.36752(18) 0.0192(6) Uani 1 2 d S . .
H3A H 0.2787 0.4013 0.4047 0.023 Uiso 0.50 1 calc PR . .
H3B H 0.2787 0.5987 0.4047 0.023 Uiso 0.50 1 calc PR . .
C7 C -0.05273(10) -0.1506(2) 0.36851(13) 0.0186(4) Uani 1 1 d . . .
H7 H -0.0309 -0.2522 0.3688 0.022 Uiso 1 1 calc R . .
C8 C -0.11976(10) -0.1502(2) 0.36466(14) 0.0201(4) Uani 1 1 d . . .
H8 H -0.1424 -0.2517 0.3626 0.024 Uiso 1 1 calc R . .
C4 C 0.34692(14) 0.5000 0.36380(17) 0.0157(5) Uani 1 2 d S . .
C1 C 0.02771(9) 0.1351(2) 0.21597(13) 0.0149(4) Uani 1 1 d . . .
H1 H 0.0319 0.2465 0.2366 0.018 Uiso 1 1 calc R . .
C5 C 0.05564(14) 0.0000 0.37886(18) 0.0145(5) Uani 1 2 d S . .
H5A H 0.0854 0.0988 0.4163 0.017 Uiso 0.50 1 calc PR . .
H5B H 0.0854 -0.0988 0.4163 0.017 Uiso 0.50 1 calc PR . .
C9 C 0.73155(16) 0.0000 0.9055(2) 0.0257(6) Uani 1 2 d S . .
C11 C 0.82961(17) 0.0000 1.0864(2) 0.0412(8) Uani 1 2 d S . .
H11A H 0.8581 0.0992 1.1251 0.049 Uiso 0.50 1 calc PR . .
H11B H 0.8581 -0.0992 1.1251 0.049 Uiso 0.50 1 calc PR . .
C12 C 0.75110(17) 0.0000 1.0666(2) 0.0356(7) Uani 1 2 d S . .
H12A H 0.7440 -0.0993 1.0959 0.043 Uiso 0.50 1 calc PR . .
H12B H 0.7440 0.0993 1.0959 0.043 Uiso 0.50 1 calc PR . .
C10 C 0.81726(17) 0.0000 0.9827(2) 0.0373(8) Uani 1 2 d S . .
H10A H 0.8399 -0.0993 0.9746 0.045 Uiso 0.50 1 calc PR . .
H10B H 0.8399 0.0993 0.9746 0.045 Uiso 0.50 1 calc PR . .
C13 C 0.61609(16) 0.0000 0.9055(2) 0.0319(7) Uani 1 2 d S . .
H13A H 0.6005 0.1058 0.9173 0.048 Uiso 0.50 1 calc PR . .
H13B H 0.6022 -0.0896 0.9325 0.048 Uiso 0.50 1 calc PR . .
H13C H 0.5912 -0.0162 0.8332 0.048 Uiso 0.50 1 calc PR . .
N5 N 0.69823(13) 0.0000 0.95607(18) 0.0261(5) Uani 1 2 d S . .
O1 O 0.69723(13) 0.0000 0.81168(16) 0.0420(6) Uani 1 2 d S . .
O4 O 0.11857(15) 0.5000 0.50508(17) 0.0452(6) Uani 1 2 d S . .
O5 O 0.76782(11) 0.0000 0.71135(15) 0.0261(4) Uani 1 2 d SD . .
H15 H 0.745(2) 0.0000 0.748(2) 0.064(13) Uiso 1 2 d SD . .
H16 H 0.7305(17) 0.0000 0.6432(14) 0.061(12) Uiso 1 2 d SD . .


_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 N3 2.2987(14) . ?
Ag1 N3 2.2987(14) 2 ?
Ag1 N1 2.2990(14) . ?
Ag1 N1 2.2990(14) 2 ?
Cl1 O4 1.423(2) . ?
Cl1 O2 1.4359(14) 6_565 ?
Cl1 O2 1.4359(14) . ?
Cl1 O3 1.4409(19) . ?
N2 C1 1.350(2) 6 ?
N2 C1 1.350(2) . ?
N2 C5 1.480(3) . ?
C6 C7 1.386(2) 6 ?
C6 C7 1.386(2) . ?
C6 C5 1.512(3) . ?
N4 C2 1.350(2) . ?
N4 C2 1.350(2) 6_565 ?
N4 C3 1.479(3) . ?
N3 C2 1.314(2) . ?
N3 N3 1.390(3) 6_565 ?
N1 C1 1.308(2) . ?
N1 N1 1.389(3) 6 ?
C3 C4 1.516(3) . ?
C7 C8 1.390(3) . ?
C8 C4 1.383(2) 3_445 ?
C4 C8 1.383(2) 8 ?
C4 C8 1.383(2) 3 ?
C9 O1 1.229(3) . ?
C9 N5 1.337(4) . ?
C9 C10 1.510(4) . ?
C11 C10 1.509(4) . ?
C11 C12 1.512(4) . ?
C12 N5 1.447(4) . ?
C13 N5 1.448(4) . ?

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
N3 Ag1 N3 112.88(7) . 2 ?
N3 Ag1 N1 92.35(5) . . ?
N3 Ag1 N1 126.15(5) 2 . ?
N3 Ag1 N1 126.15(5) . 2 ?
N3 Ag1 N1 92.35(5) 2 2 ?
N1 Ag1 N1 110.39(7) . 2 ?
O4 Cl1 O2 109.59(9) . 6_565 ?
O4 Cl1 O2 109.59(9) . . ?
O2 Cl1 O2 110.35(12) 6_565 . ?
O4 Cl1 O3 109.44(14) . . ?
O2 Cl1 O3 108.93(8) 6_565 . ?
O2 Cl1 O3 108.93(8) . . ?
C1 N2 C1 105.25(19) 6 . ?
C1 N2 C5 127.19(10) 6 . ?
C1 N2 C5 127.19(10) . . ?
C7 C6 C7 119.2(2) 6 . ?
C7 C6 C5 120.38(11) 6 . ?
C7 C6 C5 120.38(11) . . ?
C2 N4 C2 105.6(2) . 6_565 ?
C2 N4 C3 127.22(10) . . ?
C2 N4 C3 127.22(10) 6_565 . ?
C2 N3 N3 106.83(10) . 6_565 ?
C2 N3 Ag1 128.11(12) . . ?
N3 N3 Ag1 123.56(4) 6_565 . ?
C1 N1 N1 106.83(10) . 6 ?
C1 N1 Ag1 127.38(12) . . ?
N1 N1 Ag1 124.80(4) 6 . ?
N3 C2 N4 110.39(16) . . ?
N4 C3 C4 112.5(2) . . ?
C6 C7 C8 120.24(17) . . ?
C4 C8 C7 120.53(18) 3_445 . ?
C8 C4 C8 119.2(2) 8 3 ?
C8 C4 C3 120.37(11) 8 . ?
C8 C4 C3 120.37(11) 3 . ?
N1 C1 N2 110.55(16) . . ?
N2 C5 C6 110.83(19) . . ?
O1 C9 N5 125.0(3) . . ?
O1 C9 C10 126.3(3) . . ?
N5 C9 C10 108.7(2) . . ?
C10 C11 C12 106.7(2) . . ?
N5 C12 C11 104.8(2) . . ?
C11 C10 C9 105.4(2) . . ?
C9 N5 C12 114.5(2) . . ?
C9 N5 C13 123.4(2) . . ?
C12 N5 C13 122.1(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.70
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_Agrotbiph
_database_code_depnum_ccdc_archive 'CCDC 1413569'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H16 Ag Cl N9 O7'
_chemical_formula_weight         757.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   28.682(17)
_cell_length_b                   7.981(5)
_cell_length_c                   29.940(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.600(7)
_cell_angle_gamma                90.00
_cell_volume                     6661(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3032
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8475
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27593
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_av_sigmaI/netI    0.0935
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.40
_diffrn_reflns_theta_max         25.19
_reflns_number_total             5843
_reflns_number_gt                3561
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0331P)²+934.4604P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5843
_refine_ls_number_parameters     417
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1810
_refine_ls_R_factor_gt           0.1321
_refine_ls_wR_factor_ref         0.3464
_refine_ls_wR_factor_gt          0.3117
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag1 Ag 0.0000 1.0512(2) 0.2500 0.0284(5) Uani 1 2 d S . .
Ag2 Ag 0.0000 0.5485(2) 0.2500 0.0302(6) Uani 1 2 d S . .
Cl1 Cl 0.18502(13) 0.2822(6) 0.25188(16) 0.0343(10) Uani 1 1 d . . .
N2 N -0.1181(4) 0.298(2) 0.1541(5) 0.031(3) Uani 1 1 d . . .
N1 N -0.0526(5) 0.3832(18) 0.1996(5) 0.027(3) Uani 1 1 d . . .
N3 N 0.1266(5) 0.802(2) 0.2241(5) 0.030(3) Uani 1 1 d . . .
N5 N 0.0606(5) 0.718(2) 0.2375(5) 0.033(3) Uani 1 1 d . . .
N4 N 0.0578(5) 0.8838(19) 0.2334(5) 0.030(3) Uani 1 1 d . . .
C2 C 0.0986(6) 0.933(2) 0.2257(6) 0.032(3) Uani 1 1 d . . .
H2 H 0.1068 1.0442 0.2220 0.038 Uiso 1 1 calc R . .
C1 C 0.1021(6) 0.668(2) 0.2315(6) 0.032(3) Uani 1 1 d . . .
H1 H 0.1126 0.5573 0.2322 0.038 Uiso 1 1 calc R . .
C7 C 0.1626(5) 0.794(3) 0.0668(6) 0.033(4) Uani 1 1 d . . .
C3 C 0.1739(5) 0.804(3) 0.2119(5) 0.029(4) Uani 1 1 d . . .
H3A H 0.1922 0.7056 0.2248 0.034 Uiso 1 1 calc R . .
H3B H 0.1918 0.9024 0.2248 0.034 Uiso 1 1 calc R . .
C10 C 0.1614(6) 0.774(2) 0.0180(6) 0.034(4) Uani 1 1 d . . .
C9 C 0.1309(6) 0.728(3) 0.1311(7) 0.038(3) Uani 1 1 d . . .
H9 H 0.1065 0.6792 0.1424 0.045 Uiso 1 1 calc R . .
C4 C 0.1672(5) 0.804(3) 0.1609(6) 0.035(4) Uani 1 1 d . . .
C6 C 0.1983(6) 0.884(3) 0.0970(7) 0.041(5) Uani 1 1 d . . .
H6 H 0.2211 0.9416 0.0853 0.050 Uiso 1 1 calc R . .
C8 C 0.1282(6) 0.719(3) 0.0857(7) 0.047(5) Uani 1 1 d . . .
H8 H 0.1029 0.6622 0.0667 0.056 Uiso 1 1 calc R . .
C5 C 0.2010(6) 0.892(3) 0.1423(7) 0.038(3) Uani 1 1 d . . .
H5 H 0.2250 0.9543 0.1613 0.045 Uiso 1 1 calc R . .
C12 C -0.1650(5) 0.300(3) 0.1224(6) 0.036(4) Uani 1 1 d . . .
H12A H -0.1794 0.4099 0.1233 0.043 Uiso 1 1 calc R . .
H12B H -0.1855 0.2182 0.1320 0.043 Uiso 1 1 calc R . .
C11 C -0.0924(6) 0.429(3) 0.1719(6) 0.036(4) Uani 1 1 d . . .
H11 H -0.1016 0.5401 0.1654 0.043 Uiso 1 1 calc R . .
C14 C -0.1619(6) 0.263(2) 0.0741(6) 0.033(4) Uani 1 1 d . . .
C15 C -0.1938(8) 0.166(4) 0.0465(8) 0.075(9) Uani 1 1 d . . .
H15 H -0.2169 0.1112 0.0585 0.090 Uiso 1 1 calc R . .
C13 C -0.1301(10) 0.348(5) 0.0552(9) 0.104(14) Uani 1 1 d . . .
H13 H -0.1091 0.4247 0.0728 0.124 Uiso 1 1 calc R . .
C25 C 0.1964(7) 0.774(3) 0.3399(7) 0.047(5) Uani 1 1 d D . .
C27 C 0.2444(10) 0.756(3) 0.4162(11) 0.124(19) Uani 1 1 d D . .
C26 C 0.2716(8) 0.960(3) 0.3656(9) 0.062(7) Uani 1 1 d D . .
C28 C 0.2874(7) 0.829(3) 0.4531(9) 0.061(7) Uani 1 1 d . . .
O1 O 0.2178(5) 0.6485(19) 0.4230(7) 0.068(5) Uani 1 1 d . . .
N8 N 0.2397(10) 0.832(3) 0.3806(12) 0.108(7) Uani 1 1 d . . .
N6 N 0.4611(6) 0.391(2) 0.0879(6) 0.052(5) Uani 1 1 d . . .
C18 C 0.4982(8) 0.406(4) 0.1295(9) 0.072(8) Uani 1 1 d . . .
C19 C 0.3818(8) 0.297(5) 0.0477(8) 0.078(9) Uani 1 1 d . . .
C17 C 0.4707(10) 0.457(4) 0.0461(9) 0.076(8) Uani 1 1 d . . .
C23 C 0.4187(7) 0.316(3) 0.0906(7) 0.047(5) Uani 1 1 d . . .
O2 O 0.4120(5) 0.282(2) 0.1280(5) 0.051(4) Uani 1 1 d . . .
C24 C 0.0394(8) 0.388(3) 0.0962(9) 0.062(7) Uani 1 1 d . . .
C21 C 0.1041(8) 0.200(4) 0.1066(9) 0.067(7) Uani 1 1 d . . .
C20 C 0.0651(9) 0.346(3) 0.0347(6) 0.054(6) Uani 1 1 d . . .
C22 C 0.0008(11) 0.499(4) 0.0664(12) 0.088(9) Uani 1 1 d . . .
O3 O 0.0381(10) 0.366(3) 0.1449(10) 0.130(9) Uani 1 1 d . . .
N7 N 0.0670(10) 0.321(3) 0.0741(12) 0.108(7) Uani 1 1 d . . .
O4 O 0.1396(5) 0.297(2) 0.2217(6) 0.072(5) Uani 1 1 d . . .
O7 O 0.1837(7) 0.153(2) 0.2834(5) 0.065(5) Uani 1 1 d . . .
O6 O 0.1971(7) 0.436(2) 0.2738(8) 0.104(8) Uani 1 1 d . . .
O5 O 0.2180(8) 0.243(2) 0.2273(9) 0.106(8) Uani 1 1 d . . .
N9 N -0.0521(5) 0.214(2) 0.1990(5) 0.032(3) Uani 1 1 d . . .
C29 C -0.0921(6) 0.164(2) 0.1723(6) 0.030(4) Uani 1 1 d . . .
H29 H -0.1014 0.0531 0.1667 0.036 Uiso 1 1 calc R . .
C30 C 0.1295(9) 0.679(5) -0.0105(7) 0.091(12) Uani 1 1 d . . .
H30 H 0.1054 0.6285 0.0008 0.109 Uiso 1 1 calc R . .
C31 C 0.1941(8) 0.856(4) -0.0015(8) 0.075(9) Uani 1 1 d . . .
H31 H 0.2166 0.9277 0.0164 0.090 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag1 N9 2.273(15) 2_565 ?
Ag1 N9 2.273(15) 1_565 ?
Ag1 N4 2.275(13) 2 ?
Ag1 N4 2.275(13) . ?
Ag2 N1 2.286(14) . ?
Ag2 N1 2.286(14) 2 ?
Ag2 N5 2.300(14) . ?
Ag2 N5 2.300(14) 2 ?
Cl1 O5 1.364(17) . ?
Cl1 O6 1.396(16) . ?
Cl1 O7 1.403(16) . ?
Cl1 O4 1.406(14) . ?
N2 C11 1.32(2) . ?
N2 C29 1.34(2) . ?
N2 C12 1.45(2) . ?
N1 C11 1.30(2) . ?
N1 N9 1.35(2) . ?
N3 C2 1.33(2) . ?
N3 C1 1.33(2) . ?
N3 C3 1.486(18) . ?
N5 C1 1.31(2) . ?
N5 N4 1.331(19) . ?
N4 C2 1.30(2) . ?
C7 C8 1.38(2) . ?
C7 C6 1.40(3) . ?
C7 C10 1.46(2) . ?
C3 C4 1.49(2) . ?
C10 C30 1.33(3) . ?
C10 C31 1.38(3) . ?
C9 C8 1.35(3) . ?
C9 C4 1.35(2) . ?
C4 C5 1.41(2) . ?
C6 C5 1.34(3) . ?
C12 C14 1.50(2) . ?
C14 C15 1.33(3) . ?
C14 C13 1.36(3) . ?
C15 C31 1.36(3) 5_565 ?
C13 C30 1.36(3) 5_565 ?
C25 N8 1.59(4) . ?
C27 O1 1.20(3) . ?
C27 N8 1.20(4) . ?
C27 C28 1.56(4) . ?
C26 N8 1.51(3) . ?
N6 C23 1.37(3) . ?
N6 C18 1.44(3) . ?
N6 C17 1.44(3) . ?
C19 C23 1.47(3) . ?
C23 O2 1.21(2) . ?
C24 N7 1.26(3) . ?
C24 O3 1.48(3) . ?
C24 C22 1.53(4) . ?
C21 N7 1.59(4) . ?
C20 N7 1.18(4) . ?
N9 C29 1.30(2) . ?
N9 Ag1 2.273(15) 1_545 ?
C30 C13 1.36(3) 5_565 ?
C31 C15 1.36(3) 5_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
N9 Ag1 N9 110.5(8) 2_565 1_565 ?
N9 Ag1 N4 125.9(5) 2_565 2 ?
N9 Ag1 N4 94.8(5) 1_565 2 ?
N9 Ag1 N4 94.8(5) 2_565 . ?
N9 Ag1 N4 125.9(5) 1_565 . ?
N4 Ag1 N4 108.0(7) 2 . ?
N1 Ag2 N1 109.5(7) . 2 ?
N1 Ag2 N5 129.6(5) . . ?
N1 Ag2 N5 92.3(5) 2 . ?
N1 Ag2 N5 92.3(5) . 2 ?
N1 Ag2 N5 129.6(5) 2 2 ?
N5 Ag2 N5 108.1(8) . 2 ?
O5 Cl1 O6 109.3(14) . . ?
O5 Cl1 O7 108.9(11) . . ?
O6 Cl1 O7 111.7(12) . . ?
O5 Cl1 O4 109.1(15) . . ?
O6 Cl1 O4 108.5(11) . . ?
O7 Cl1 O4 109.2(11) . . ?
C11 N2 C29 105.3(14) . . ?
C11 N2 C12 126.5(18) . . ?
C29 N2 C12 128.2(17) . . ?
C11 N1 N9 106.6(15) . . ?
C11 N1 Ag2 127.1(13) . . ?
N9 N1 Ag2 125.3(11) . . ?
C2 N3 C1 106.4(13) . . ?
C2 N3 C3 126.9(16) . . ?
C1 N3 C3 126.6(16) . . ?
C1 N5 N4 109.1(14) . . ?
C1 N5 Ag2 126.2(13) . . ?
N4 N5 Ag2 124.7(11) . . ?
C2 N4 N5 106.4(14) . . ?
C2 N4 Ag1 126.2(13) . . ?
N5 N4 Ag1 126.5(11) . . ?
N4 C2 N3 110.1(16) . . ?
N5 C1 N3 108.1(16) . . ?
C8 C7 C6 116.2(17) . . ?
C8 C7 C10 120.7(17) . . ?
C6 C7 C10 123.1(16) . . ?
N3 C3 C4 110.2(12) . . ?
C30 C10 C31 115.5(19) . . ?
C30 C10 C7 123.6(17) . . ?
C31 C10 C7 120.9(17) . . ?
C8 C9 C4 123.0(16) . . ?
C9 C4 C5 117.2(17) . . ?
C9 C4 C3 124.8(16) . . ?
C5 C4 C3 117.9(16) . . ?
C5 C6 C7 122.5(17) . . ?
C9 C8 C7 121.0(18) . . ?
C6 C5 C4 119.7(17) . . ?
N2 C12 C14 111.8(13) . . ?
N1 C11 N2 110.9(18) . . ?
C15 C14 C13 118(2) . . ?
C15 C14 C12 121.8(16) . . ?
C13 C14 C12 119.8(19) . . ?
C14 C15 C31 122(2) . 5_565 ?
C30 C13 C14 120(2) 5_565 . ?
O1 C27 N8 124(4) . . ?
O1 C27 C28 125(3) . . ?
N8 C27 C28 110(2) . . ?
C27 N8 C26 131(3) . . ?
C27 N8 C25 116(2) . . ?
C26 N8 C25 113(3) . . ?
C23 N6 C18 118.1(19) . . ?
C23 N6 C17 124(2) . . ?
C18 N6 C17 118(2) . . ?
O2 C23 N6 119(2) . . ?
O2 C23 C19 123(2) . . ?
N6 C23 C19 117(2) . . ?
N7 C24 O3 129(3) . . ?
N7 C24 C22 113(3) . . ?
O3 C24 C22 117(2) . . ?
C20 N7 C24 124(3) . . ?
C20 N7 C21 125(2) . . ?
C24 N7 C21 110(3) . . ?
C29 N9 N1 107.5(14) . . ?
C29 N9 Ag1 126.0(13) . 1_545 ?
N1 N9 Ag1 124.7(12) . 1_545 ?
N9 C29 N2 109.7(15) . . ?
C10 C30 C13 124(2) . 5_565 ?
C15 C31 C10 121(2) 5_565 . ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.19
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         5.178
_refine_diff_density_min         -6.618
_refine_diff_density_rms         0.267
####################################################################### 
# 
# 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_Cubiphenyl
_database_code_depnum_ccdc_archive 'CCDC 1413570'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cl Cu N6 O4'
_chemical_formula_weight         479.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/m'

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

_cell_length_a                   23.950(4)
_cell_length_b                   7.2064(11)
_cell_length_c                   18.712(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.580(3)
_cell_angle_gamma                90.00
_cell_volume                     2690.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7990
_exptl_absorpt_correction_T_max  0.9907
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS Smart APEX II'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22310
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         24.88
_reflns_number_total             2523
_reflns_number_gt                2030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1407P)²+16.0657P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2523
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2507
_refine_ls_wR_factor_gt          0.2363
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.24939(11) 1.0000 0.0404(4) Uani 1 2 d S . .
N7 N 0.0436(3) 0.5000 0.8378(4) 0.0351(14) Uani 1 2 d S . .
N9 N 0.1857(3) 0.0000 1.1025(4) 0.0353(14) Uani 1 2 d S . .
N6 N 0.0090(2) 0.4052(6) 0.9175(3) 0.0353(10) Uani 1 1 d . . .
N8 N 0.0844(2) 0.0961(6) 1.0528(3) 0.0373(10) Uani 1 1 d . . .
C24 C -0.0761(6) 0.5000 0.5119(6) 0.0707(13) Uani 1 2 d S . .
C21 C 0.0174(6) 0.5000 0.6893(6) 0.0707(13) Uani 1 2 d S . .
C25 C -0.1221(4) 0.5000 0.4164(5) 0.0403(18) Uani 1 2 d S . .
C19 C 0.0299(3) 0.3540(8) 0.8694(4) 0.0467(13) Uani 1 1 d . . .
H19 H 0.0348 0.2312 0.8584 0.056 Uiso 1 1 calc R . .
C20 C 0.0715(4) 0.5000 0.7842(5) 0.0428(19) Uani 1 2 d S . .
H20A H 0.0995 0.3912 0.7978 0.051 Uiso 0.50 1 calc PR . .
H20B H 0.0995 0.6088 0.7978 0.051 Uiso 0.50 1 calc PR . .
C23 C -0.0534(4) 0.6592(10) 0.5568(4) 0.0707(13) Uani 1 1 d . . .
H23 H -0.0702 0.7715 0.5282 0.085 Uiso 1 1 calc R . .
C26 C -0.1431(5) 0.6590(10) 0.3701(4) 0.082(3) Uani 1 1 d . . .
H26 H -0.1312 0.7717 0.3991 0.098 Uiso 1 1 calc R . .
C22 C -0.0053(4) 0.6607(10) 0.6454(4) 0.0707(13) Uani 1 1 d . . .
H22 H 0.0110 0.7731 0.6741 0.085 Uiso 1 1 calc R . .
C28 C 0.2589(4) 0.0000 1.1390(5) 0.0426(18) Uani 1 2 d S . .
H28A H 0.2704 0.1090 1.1193 0.051 Uiso 0.50 1 calc PR . .
H28B H 0.2704 -0.1090 1.1193 0.051 Uiso 0.50 1 calc PR . .
C27 C 0.1460(3) 0.1450(8) 1.0823(4) 0.0445(13) Uani 1 1 d . . .
H27 H 0.1602 0.2674 1.0884 0.053 Uiso 1 1 calc R . .
C29 C 0.2986(4) 0.0000 1.2366(5) 0.0405(18) Uani 1 2 d S . .
C30 C 0.3185(5) 0.1607(10) 1.2814(4) 0.081(3) Uani 1 1 d . . .
H30 H 0.3064 0.2733 1.2523 0.097 Uiso 1 1 calc R . .
Cl2 Cl 0.33147(16) 0.5000 0.11374(16) 0.0660(8) Uani 1 2 d S . .
O9 O 0.3251(2) 0.3380(7) 0.0675(3) 0.0640(12) Uani 1 1 d . . .
O7 O 0.3945(7) 0.5000 0.1887(5) 0.157(6) Uani 1 2 d S . .
O8 O 0.2726(5) 0.5000 0.1227(6) 0.094(3) Uani 1 2 d S . .


_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
Cu1 N6 2.015(4) 2_557 ?
Cu1 N6 2.015(4) . ?
Cu1 N8 2.019(4) 2_557 ?
Cu1 N8 2.019(4) . ?
N7 C19 1.332(7) 6_565 ?
N7 C19 1.332(7) . ?
N7 C20 1.482(9) . ?
N9 C27 1.320(7) 6 ?
N9 C27 1.320(7) . ?
N9 C28 1.486(10) . ?
N6 C19 1.303(7) . ?
N6 N6 1.367(9) 6_565 ?
N8 C27 1.305(7) . ?
N8 N8 1.386(8) 6 ?
C24 C23 1.346(8) . ?
C24 C23 1.346(8) 6_565 ?
C24 C25 1.493(11) . ?
C21 C22 1.348(8) 6_565 ?
C21 C22 1.348(8) . ?
C21 C20 1.512(11) . ?
C25 C26 1.355(8) 6_565 ?
C25 C26 1.355(8) . ?
C23 C22 1.401(9) . ?
C26 C30 1.383(9) 3_454 ?
C28 C29 1.523(10) . ?
C29 C30 1.352(8) . ?
C29 C30 1.352(8) 6 ?
C30 C26 1.383(9) 3_546 ?
Cl2 O7 1.380(11) . ?
Cl2 O9 1.410(5) . ?
Cl2 O9 1.410(5) 6_565 ?
Cl2 O8 1.509(9) . ?

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
N6 Cu1 N6 112.3(2) 2_557 . ?
N6 Cu1 N8 100.19(17) 2_557 2_557 ?
N6 Cu1 N8 115.64(17) . 2_557 ?
N6 Cu1 N8 115.64(17) 2_557 . ?
N6 Cu1 N8 100.19(17) . . ?
N8 Cu1 N8 113.7(2) 2_557 . ?
C19 N7 C19 104.3(6) 6_565 . ?
C19 N7 C20 127.8(3) 6_565 . ?
C19 N7 C20 127.8(3) . . ?
C27 N9 C27 104.7(6) 6 . ?
C27 N9 C28 127.7(3) 6 . ?
C27 N9 C28 127.7(3) . . ?
C19 N6 N6 106.4(3) . 6_565 ?
C19 N6 Cu1 128.1(4) . . ?
N6 N6 Cu1 123.86(12) 6_565 . ?
C27 N8 N8 105.6(3) . 6 ?
C27 N8 Cu1 130.6(4) . . ?
N8 N8 Cu1 123.17(12) 6 . ?
C23 C24 C23 116.9(8) . 6_565 ?
C23 C24 C25 121.5(4) . . ?
C23 C24 C25 121.5(4) 6_565 . ?
C22 C21 C22 118.4(8) 6_565 . ?
C22 C21 C20 120.7(4) 6_565 . ?
C22 C21 C20 120.7(4) . . ?
C26 C25 C26 115.5(7) 6_565 . ?
C26 C25 C24 122.2(4) 6_565 . ?
C26 C25 C24 122.2(4) . . ?
N6 C19 N7 111.4(5) . . ?
N7 C20 C21 112.4(7) . . ?
C24 C23 C22 121.9(7) . . ?
C25 C26 C30 122.7(6) . 3_454 ?
C21 C22 C23 120.3(7) . . ?
N9 C28 C29 110.3(6) . . ?
N8 C27 N9 112.0(5) . . ?
C30 C29 C30 117.8(7) . 6 ?
C30 C29 C28 121.0(4) . . ?
C30 C29 C28 121.0(4) 6 . ?
C29 C30 C26 120.6(6) . 3_546 ?
O7 Cl2 O9 108.0(4) . . ?
O7 Cl2 O9 108.0(4) . 6_565 ?
O9 Cl2 O9 111.8(4) . 6_565 ?
O7 Cl2 O8 116.8(8) . . ?
O9 Cl2 O8 106.1(3) . . ?
O9 Cl2 O8 106.1(3) 6_565 . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        24.88
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.791
_refine_diff_density_min         -1.564
_refine_diff_density_rms         0.128

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.750 -0.076 0.500 431 84 ' '
2 0.250 -0.068 0.500 431 84 ' '
3 1.000 0.000 0.500 38 0 ' '
4 0.500 0.500 0.500 38 0 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_AgbiphaddNMP
_database_code_depnum_ccdc_archive 'CCDC 1413571'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 Ag Cl N7 O5'
_chemical_formula_weight         622.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/m'

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

_cell_length_a                   30.13(6)
_cell_length_b                   7.841(11)
_cell_length_c                   15.831(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.48
_cell_angle_gamma                90.00
_cell_volume                     3190(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1264
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.998
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13662
_diffrn_reflns_av_R_equivalents  0.1579
_diffrn_reflns_av_sigmaI/netI    0.1485
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         26.14
_reflns_number_total             3405
_reflns_number_gt                2020
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3405
_refine_ls_number_parameters     158
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.1955
_refine_ls_R_factor_gt           0.1449
_refine_ls_wR_factor_ref         0.4073
_refine_ls_wR_factor_gt          0.3884
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_restrained_S_all      1.349
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ag2 Ag 0.5000 0.2526(2) 1.0000 0.0279(5) Uani 1 2 d S . .
N4 N 0.4937(4) 0.0917(14) 0.8715(8) 0.024(2) Uani 1 1 d . . .
N3 N 0.3657(6) 0.5000 0.9995(12) 0.024(2) Uani 1 2 d S . .
N5 N 0.5116(6) 0.0000 0.7593(12) 0.027(4) Uiso 1 2 d S . .
N2 N 0.4306(4) 0.4083(14) 0.9831(8) 0.026(3) Uani 1 1 d . . .
C11 C 0.5044(6) 0.1391(19) 0.8029(10) 0.028(3) Uani 1 1 d . . .
H11 H 0.5066 0.2517 0.7870 0.034 Uiso 1 1 calc R . .
C12 C 0.5217(8) 0.0000 0.6743(14) 0.026(4) Uiso 1 2 d S . .
H12A H 0.5416 0.1003 0.6786 0.031 Uiso 0.50 1 calc PR . .
H12B H 0.5416 -0.1003 0.6786 0.031 Uiso 0.50 1 calc PR . .
C1 C 0.3945(5) 0.3532(18) 0.9982(10) 0.032(3) Uani 1 1 d D . .
H1 H 0.3883 0.2401 1.0066 0.038 Uiso 1 1 calc R . .
Cl1 Cl 0.0685(2) 0.0000 0.7290(4) 0.0401(14) Uani 1 2 d S . .
O4 O 0.0969(4) 0.1507(17) 0.7836(8) 0.048(3) Uani 1 1 d . . .
O3 O 0.0151(9) 0.0000 0.7191(15) 0.064(6) Uani 1 2 d S . .
O2 O 0.0623(10) 0.0000 0.6307(14) 0.071(6) Uani 1 2 d S . .
C22 C 0.3143(8) 0.5000 0.9980(13) 0.037(5) Uiso 1 2 d SD . .
H22A H 0.3139 0.4003 1.0338 0.044 Uiso 0.50 1 calc PR . .
H22B H 0.3139 0.5997 1.0338 0.044 Uiso 0.50 1 calc PR . .
O5 O 0.3282(7) 0.0000 0.9461(14) 0.062(5) Uani 1 2 d SD . .
C19 C 0.2345(11) 0.0000 0.812(2) 0.120(16) Uiso 1 2 d SD . .
H19A H 0.2239 -0.1005 0.8332 0.144 Uiso 0.50 1 calc PR . .
H19B H 0.2239 0.1005 0.8332 0.144 Uiso 0.50 1 calc PR . .
C16 C 0.3535(10) 0.0000 0.798(2) 0.085(10) Uiso 1 2 d SD . .
H16A H 0.3502 0.0000 0.7339 0.127 Uiso 1 2 calc SR . .
H16B H 0.3721 -0.1000 0.8337 0.127 Uiso 0.50 1 calc PR . .
H16C H 0.3721 0.1000 0.8337 0.127 Uiso 0.50 1 calc PR . .
C15 C 0.2932(10) 0.0000 0.8571(17) 0.24(4) Uiso 1 2 d SD . .
C17 C 0.2534(12) 0.0000 0.681(2) 0.102(13) Uiso 1 2 d SD . .
H17A H 0.2518 0.1008 0.6438 0.122 Uiso 0.50 1 calc PR . .
H17B H 0.2518 -0.1008 0.6438 0.122 Uiso 0.50 1 calc PR . .
N1 N 0.3028(11) 0.0000 0.785(2) 0.172(19) Uiso 1 2 d SD . .
C18 C 0.2106(12) 0.0000 0.703(2) 0.24(4) Uiso 1 2 d SD . .
H18A H 0.1890 -0.1003 0.6738 0.293 Uiso 0.50 1 calc PR . .
H18B H 0.1890 0.1003 0.6738 0.293 Uiso 0.50 1 calc PR . .
C32 C 0.4474(8) 0.154(3) 0.5296(17) 0.087(9) Uani 1 1 d . . .
H32 H 0.4623 0.2585 0.5573 0.105 Uiso 1 1 calc R . .
C45 C 0.1719(6) 0.5000 0.7159(14) 0.037(5) Uani 1 2 d SD . .
C42 C 0.2654(7) 0.5000 0.8979(13) 0.036(5) Uani 1 2 d SDU . .
C41 C 0.2193(8) 0.5000 0.895(2) 0.103(9) Uani 1 2 d SD . .
H41 H 0.2184 0.5000 0.9532 0.123 Uiso 1 2 calc SR . .
C46 C 0.1742(10) 0.5000 0.8034(15) 0.117(14) Uani 1 2 d SD . .
H46 H 0.1428 0.5000 0.8014 0.141 Uiso 1 2 calc SR . .
C47 C 0.4703(8) 0.0000 0.5770(15) 0.028(3) Uani 1 2 d S . .
C49 C 0.3775(8) 0.0000 0.3864(15) 0.028(3) Uani 1 2 d SU . .
C48 C 0.4009(11) 0.141(4) 0.438(2) 0.121(11) Uani 1 1 d U . .
H48 H 0.3840 0.2430 0.4100 0.145 Uiso 1 1 calc R . .
C52 C 0.2163(6) 0.5000 0.7168(13) 0.117(14) Uani 1 2 d SD . .
H52 H 0.2170 0.5000 0.6587 0.141 Uiso 1 2 calc SR . .
C53 C 0.2616(7) 0.5000 0.8095(12) 0.103(9) Uani 1 2 d SDU . .
H53 H 0.2927 0.5000 0.8105 0.123 Uiso 1 2 calc SR . .


_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
Ag2 N2 2.314(12) . ?
Ag2 N2 2.314(12) 2_657 ?
Ag2 N4 2.316(10) . ?
Ag2 N4 2.316(10) 2_657 ?
N4 C11 1.336(16) . ?
N4 N4 1.44(2) 6 ?
N3 C1 1.449(17) 6_565 ?
N3 C1 1.449(16) . ?
N3 C22 1.53(3) . ?
N5 C11 1.368(16) . ?
N5 C11 1.368(16) 6 ?
N5 C12 1.53(3) . ?
N2 C1 1.302(17) . ?
N2 N2 1.44(2) 6_565 ?
C11 H11 0.9300 . ?
C12 C47 1.51(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C1 H1 0.9300 . ?
Cl1 O4 1.450(13) . ?
Cl1 O4 1.450(13) 6 ?
Cl1 O2 1.467(19) . ?
Cl1 O3 1.53(2) . ?
C22 C42 1.50(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
O5 C15 1.243(17) . ?
C19 C18 1.497(19) . ?
C19 C15 1.523(18) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C16 N1 1.434(18) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 N1 1.317(18) . ?
C17 C18 1.496(19) . ?
C17 N1 1.54(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C32 C47 1.40(2) . ?
C32 C48 1.40(3) . ?
C32 H32 0.9300 . ?
C45 C52 1.330(17) . ?
C45 C46 1.351(17) . ?
C45 C49 1.52(3) 7_556 ?
C42 C53 1.343(17) . ?
C42 C41 1.369(18) . ?
C41 C46 1.378(18) . ?
C41 H41 0.9300 . ?
C46 H46 0.9300 . ?
C47 C32 1.40(2) 6 ?
C49 C48 1.34(3) . ?
C49 C48 1.34(3) 6 ?
C49 C45 1.52(3) 7_556 ?
C48 H48 0.9300 . ?
C52 C53 1.386(15) . ?
C52 H52 0.9300 . ?
C53 H53 0.9300 . ?

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 Ag2 N2 116.3(6) . 2_657 ?
N2 Ag2 N4 122.1(4) . . ?
N2 Ag2 N4 92.5(4) 2_657 . ?
N2 Ag2 N4 92.5(4) . 2_657 ?
N2 Ag2 N4 122.1(4) 2_657 2_657 ?
N4 Ag2 N4 114.0(6) . 2_657 ?
C11 N4 N4 106.2(8) . 6 ?
C11 N4 Ag2 128.2(9) . . ?
N4 N4 Ag2 123.0(3) 6 . ?
C1 N3 C1 105.2(15) 6_565 . ?
C1 N3 C22 127.4(7) 6_565 . ?
C1 N3 C22 127.4(7) . . ?
C11 N5 C11 105.8(15) . 6 ?
C11 N5 C12 127.1(8) . . ?
C11 N5 C12 127.1(8) 6 . ?
C1 N2 N2 109.4(8) . 6_565 ?
C1 N2 Ag2 126.5(10) . . ?
N2 N2 Ag2 121.8(3) 6_565 . ?
N4 C11 N5 111.0(12) . . ?
N4 C11 H11 124.5 . . ?
N5 C11 H11 124.5 . . ?
C47 C12 N5 109.2(15) . . ?
C47 C12 H12A 109.8 . . ?
N5 C12 H12A 109.8 . . ?
C47 C12 H12B 109.8 . . ?
N5 C12 H12B 109.8 . . ?
H12A C12 H12B 108.3 . . ?
N2 C1 N3 107.7(12) . . ?
N2 C1 H1 126.2 . . ?
N3 C1 H1 126.2 . . ?
O4 Cl1 O4 109.1(10) . 6 ?
O4 Cl1 O2 110.0(7) . . ?
O4 Cl1 O2 110.0(7) 6 . ?
O4 Cl1 O3 108.8(7) . . ?
O4 Cl1 O3 108.8(7) 6 . ?
O2 Cl1 O3 110.2(13) . . ?
C42 C22 N3 116.3(14) . . ?
C42 C22 H22A 108.2 . . ?
N3 C22 H22A 108.2 . . ?
C42 C22 H22B 108.2 . . ?
N3 C22 H22B 108.2 . . ?
H22A C22 H22B 107.4 . . ?
C18 C19 C15 106.0(16) . . ?
C18 C19 H19A 110.5 . . ?
C15 C19 H19A 110.5 . . ?
C18 C19 H19B 110.5 . . ?
C15 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C15 N1 123(2) . . ?
O5 C15 C19 128(2) . . ?
N1 C15 C19 108.9(17) . . ?
C18 C17 N1 102.8(17) . . ?
C18 C17 H17A 111.2 . . ?
N1 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
N1 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C15 N1 C16 125(3) . . ?
C15 N1 C17 113.7(17) . . ?
C16 N1 C17 121(2) . . ?
C17 C18 C19 108.6(18) . . ?
C17 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
C17 C18 H18B 110.0 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C47 C32 C48 116(2) . . ?
C47 C32 H32 121.9 . . ?
C48 C32 H32 121.9 . . ?
C52 C45 C46 118.5(18) . . ?
C52 C45 C49 115.6(15) . 7_556 ?
C46 C45 C49 125.9(16) . 7_556 ?
C53 C42 C41 115.8(18) . . ?
C53 C42 C22 127.2(16) . . ?
C41 C42 C22 117.0(17) . . ?
C42 C41 C46 117(2) . . ?
C42 C41 H41 121.4 . . ?
C46 C41 H41 121.4 . . ?
C45 C46 C41 125(2) . . ?
C45 C46 H46 117.4 . . ?
C41 C46 H46 117.4 . . ?
C32 C47 C32 119(2) 6 . ?
C32 C47 C12 120.3(11) 6 . ?
C32 C47 C12 120.3(11) . . ?
C48 C49 C48 111(3) . 6 ?
C48 C49 C45 124.3(13) . 7_556 ?
C48 C49 C45 124.2(13) 6 7_556 ?
C49 C48 C32 128(2) . . ?
C49 C48 H48 115.9 . . ?
C32 C48 H48 115.9 . . ?
C45 C52 C53 116.0(17) . . ?
C45 C52 H52 122.0 . . ?
C53 C52 H52 122.0 . . ?
C42 C53 C52 127.3(18) . . ?
C42 C53 H53 116.4 . . ?
C52 C53 H53 116.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ag2 N4 C11 91.5(12) . . . . ?
N2 Ag2 N4 C11 -32.0(12) 2_657 . . . ?
N4 Ag2 N4 C11 -158.9(13) 2_657 . . . ?
N2 Ag2 N4 N4 -109.6(4) . . . 6 ?
N2 Ag2 N4 N4 127.0(3) 2_657 . . 6 ?
N4 Ag2 N4 N4 0.000(6) 2_657 . . 6 ?
N2 Ag2 N2 C1 -160.9(12) 2_657 . . . ?
N4 Ag2 N2 C1 87.5(12) . . . . ?
N4 Ag2 N2 C1 -33.0(11) 2_657 . . . ?
N2 Ag2 N2 N2 0.0 2_657 . . 6_565 ?
N4 Ag2 N2 N2 -111.6(4) . . . 6_565 ?
N4 Ag2 N2 N2 128.0(3) 2_657 . . 6_565 ?
N4 N4 C11 N5 -0.4(13) 6 . . . ?
Ag2 N4 C11 N5 161.3(10) . . . . ?
C11 N5 C11 N4 1(2) 6 . . . ?
C12 N5 C11 N4 176.7(15) . . . . ?
C11 N5 C12 C47 -87.6(16) . . . . ?
C11 N5 C12 C47 87.6(16) 6 . . . ?
N2 N2 C1 N3 5.3(12) 6_565 . . . ?
Ag2 N2 C1 N3 168.2(9) . . . . ?
C1 N3 C1 N2 -8.3(18) 6_565 . . . ?
C22 N3 C1 N2 169.3(15) . . . . ?
C1 N3 C22 C42 88.5(15) 6_565 . . . ?
C1 N3 C22 C42 -88.5(15) . . . . ?
C18 C19 C15 O5 180.000(10) . . . . ?
C18 C19 C15 N1 0.000(8) . . . . ?
O5 C15 N1 C16 0.000(14) . . . . ?
C19 C15 N1 C16 180.000(12) . . . . ?
O5 C15 N1 C17 180.000(10) . . . . ?
C19 C15 N1 C17 0.000(9) . . . . ?
C18 C17 N1 C15 0.000(6) . . . . ?
C18 C17 N1 C16 180.000(10) . . . . ?
N1 C17 C18 C19 0.000(9) . . . . ?
C15 C19 C18 C17 0.000(8) . . . . ?
N3 C22 C42 C53 0.000(8) . . . . ?
N3 C22 C42 C41 180.000(9) . . . . ?
C53 C42 C41 C46 0.000(8) . . . . ?
C22 C42 C41 C46 180.000(7) . . . . ?
C52 C45 C46 C41 0.000(8) . . . . ?
C49 C45 C46 C41 180.000(10) 7_556 . . . ?
C42 C41 C46 C45 0.000(12) . . . . ?
C48 C32 C47 C32 3(5) . . . 6 ?
C48 C32 C47 C12 178(2) . . . . ?
N5 C12 C47 C32 -93(2) . . . 6 ?
N5 C12 C47 C32 93(2) . . . . ?
C48 C49 C48 C32 8(6) 6 . . . ?
C45 C49 C48 C32 -176(3) 7_556 . . . ?
C47 C32 C48 C49 -6(5) . . . . ?
C46 C45 C52 C53 0.000(6) . . . . ?
C49 C45 C52 C53 180.000(5) 7_556 . . . ?
C41 C42 C53 C52 0.000(6) . . . . ?
C22 C42 C53 C52 180.000(8) . . . . ?
C45 C52 C53 C42 0.000(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.14
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         4.907
_refine_diff_density_min         -2.477
_refine_diff_density_rms         0.282

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 -0.047 0.500 416 172 ' '
2 0.750 -0.042 0.500 416 172 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_Cunaphthyl
_database_code_depnum_ccdc_archive 'CCDC 1413572'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cl Cu N6 O4'
_chemical_formula_weight         453.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2'

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

_cell_length_a                   24.851(16)
_cell_length_b                   7.517(5)
_cell_length_c                   16.975(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 130.638(6)
_cell_angle_gamma                90.00
_cell_volume                     2406(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS Smart APEX II'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5305
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0838
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         20.21
_reflns_number_total             2287
_reflns_number_gt                1617
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.35(13)
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     102
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.1092
_refine_ls_wR_factor_ref         0.3255
_refine_ls_wR_factor_gt          0.2995
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_restrained_S_all      1.225
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 0.4954(2) 0.5816(12) 0.0882(4) 0.060(6) Uiso 1 1 d G . .
C4 C 0.4690(4) 0.5216(12) 0.1367(6) 0.081(9) Uiso 1 1 d GD . .
H4 H 0.4601 0.4039 0.1421 0.097 Uiso 1 1 calc R . .
N6 N 0.4585(4) 0.6727(13) 0.1756(6) 0.049(3) Uiso 1 1 d G . .
C5 C 0.4785(4) 0.8261(12) 0.1511(6) 0.035(5) Uiso 1 1 d GD . .
H5 H 0.4769 0.9429 0.1676 0.042 Uiso 1 1 calc R . .
N5 N 0.5013(4) 0.7698(12) 0.0971(6) 0.025(4) Uiso 1 1 d G . .
N1 N 0.5857(4) 0.0860(12) 0.0621(6) 0.028(4) Uiso 1 1 d G . .
C1 C 0.6444(4) 0.0318(13) 0.0813(5) 0.107(11) Uiso 1 1 d G . .
H1 H 0.6553 -0.0838 0.0764 0.128 Uiso 1 1 calc R . .
N3 N 0.6865(3) 0.1848(14) 0.1103(6) 0.044(3) Uani 1 1 d G . .
C2 C 0.6509(3) 0.3203(13) 0.0980(5) 0.014(4) Uiso 1 1 d G . .
H2 H 0.6669 0.4374 0.1127 0.017 Uiso 1 1 calc R . .
N2 N 0.5818(3) 0.2614(12) 0.0573(3) 0.058(6) Uiso 1 1 d G . .
C54 C 0.5324(6) 0.5564(17) 0.4171(7) 0.074(7) Uiso 1 1 d G . .
H54 H 0.5226 0.4401 0.3925 0.089 Uiso 1 1 calc R . .
C50 C 0.4962(5) 0.697(2) 0.3479(6) 0.059(5) Uiso 1 1 d G . .
C57 C 0.5109(7) 0.8710(19) 0.3846(9) 0.122(11) Uiso 1 1 d G . .
H57 H 0.4867 0.9652 0.3383 0.146 Uiso 1 1 calc R . .
C58 C 0.5617(7) 0.9040(14) 0.4905(10) 0.174(17) Uiso 1 1 d G . .
H58 H 0.5715 1.0203 0.5151 0.209 Uiso 1 1 calc R . .
C56 C 0.5979(5) 0.7633(13) 0.5597(7) 0.052(6) Uiso 1 1 d G . .
C55 C 0.5832(4) 0.5895(13) 0.5230(6) 0.049(6) Uiso 1 1 d G . .
C60 C 0.6194(7) 0.4487(14) 0.5922(8) 0.138(12) Uiso 1 1 d G . .
H60 H 0.6096 0.3324 0.5677 0.165 Uiso 1 1 calc R . .
C62 C 0.6702(6) 0.4818(18) 0.6981(8) 0.092(8) Uiso 1 1 d G . .
H62 H 0.6945 0.3876 0.7445 0.110 Uiso 1 1 calc R . .
C61 C 0.6849(5) 0.656(2) 0.7349(6) 0.056(5) Uiso 1 1 d G . .
C59 C 0.6487(6) 0.7963(17) 0.6657(7) 0.097(8) Uiso 1 1 d G . .
H59 H 0.6585 0.9126 0.6902 0.117 Uiso 1 1 calc R . .
Cu1 Cu 0.5000 -0.0705(3) 0.0000 0.0370(11) Uani 1 2 d S . .
Cu2 Cu 0.5000 0.4257(3) 0.0000 0.0357(11) Uani 1 2 d S . .
Cl3 Cl 0.3612(4) 0.1815(16) 0.1489(5) 0.107(2) Uani 1 1 d . . .
C3 C 0.7584(8) 0.192(3) 0.1474(11) 0.047(4) Uiso 1 1 d . . .
H3A H 0.7666 0.3088 0.1326 0.056 Uiso 1 1 calc R . .
H3B H 0.7631 0.1049 0.1101 0.056 Uiso 1 1 calc R . .
C6 C 0.4378(7) 0.663(3) 0.2369(9) 0.036(4) Uiso 1 1 d D . .
H6A H 0.4185 0.5459 0.2289 0.043 Uiso 1 1 calc R . .
H6B H 0.4004 0.7493 0.2106 0.043 Uiso 1 1 calc R . .
O2 O 0.3308(12) 0.016(3) 0.1027(16) 0.104(7) Uani 1 1 d . . .
O1 O 0.3356(9) 0.324(2) 0.0873(13) 0.069(5) Uani 1 1 d . . .
O4 O 0.4380(7) 0.160(3) 0.1914(13) 0.101(5) Uani 1 1 d . . .
O3 O 0.3734(15) 0.209(3) 0.2396(16) 0.150(10) 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
N4 C4 1.4200 . ?
N4 N5 1.4200 . ?
N4 Cu2 1.962(7) . ?
C4 N6 1.4200 . ?
N6 C5 1.4200 . ?
N6 C6 1.433(11) . ?
C5 N5 1.4200 . ?
N5 Cu1 2.023(8) 1_565 ?
N1 N2 1.3210 . ?
N1 C1 1.3340 . ?
N1 Cu1 2.026(8) . ?
C1 N3 1.4099 . ?
N3 C2 1.2732 . ?
N3 C3 1.458(16) . ?
C2 N2 1.4427 . ?
N2 Cu2 2.007(7) . ?
C54 C50 1.3900 . ?
C54 C55 1.3900 . ?
C50 C57 1.3900 . ?
C50 C6 1.470(15) . ?
C57 C58 1.3900 . ?
C58 C56 1.3900 . ?
C56 C55 1.3900 . ?
C56 C59 1.3900 . ?
C55 C60 1.3900 . ?
C60 C62 1.3900 . ?
C62 C61 1.3900 . ?
C61 C59 1.3900 . ?
C61 C3 1.545(16) 4_656 ?
Cu1 N5 2.023(16) 1_545 ?
Cu1 N5 2.02(2) 2_645 ?
Cu1 N1 2.026(7) 2_655 ?
Cu2 N4 1.962(7) 2_655 ?
Cu2 N2 2.007(9) 2_655 ?
Cl3 O1 1.332(16) . ?
Cl3 O3 1.378(17) . ?
Cl3 O2 1.403(19) . ?
Cl3 O4 1.550(15) . ?
C3 C61 1.54(4) 4_646 ?

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
C4 N4 N5 108.0 . . ?
C4 N4 Cu2 122.1(3) . . ?
N5 N4 Cu2 128.5(3) . . ?
N4 C4 N6 108.0 . . ?
C5 N6 C4 108.0 . . ?
C5 N6 C6 127.8(9) . . ?
C4 N6 C6 124.0(9) . . ?
N5 C5 N6 108.0 . . ?
C5 N5 N4 108.0 . . ?
C5 N5 Cu1 123.2(3) . 1_565 ?
N4 N5 Cu1 123.9(4) . 1_565 ?
N2 N1 C1 110.2 . . ?
N2 N1 Cu1 122.5(3) . . ?
C1 N1 Cu1 124.1(3) . . ?
N1 C1 N3 106.3 . . ?
C2 N3 C1 108.5 . . ?
C2 N3 C3 124.3(11) . . ?
C1 N3 C3 127.1(11) . . ?
N3 C2 N2 108.4 . . ?
N1 N2 C2 105.1 . . ?
N1 N2 Cu2 130.9(3) . . ?
C2 N2 Cu2 123.9(3) . . ?
C50 C54 C55 120.0 . . ?
C57 C50 C54 120.0 . . ?
C57 C50 C6 119.3(12) . . ?
C54 C50 C6 120.4(12) . . ?
C58 C57 C50 120.0 . . ?
C56 C58 C57 120.0 . . ?
C55 C56 C58 120.0 . . ?
C55 C56 C59 120.0 . . ?
C58 C56 C59 120.0 . . ?
C60 C55 C56 120.0 . . ?
C60 C55 C54 120.0 . . ?
C56 C55 C54 120.0 . . ?
C62 C60 C55 120.0 . . ?
C60 C62 C61 120.0 . . ?
C62 C61 C59 120.0 . . ?
C62 C61 C3 119.9(12) . 4_656 ?
C59 C61 C3 120.1(13) . 4_656 ?
C61 C59 C56 120.0 . . ?
N5 Cu1 N5 107.2(6) 1_545 2_645 ?
N5 Cu1 N1 102.8(5) 1_545 2_655 ?
N5 Cu1 N1 117.8(7) 2_645 2_655 ?
N5 Cu1 N1 117.8(7) 1_545 . ?
N5 Cu1 N1 102.8(3) 2_645 . ?
N1 Cu1 N1 109.0(6) 2_655 . ?
N4 Cu2 N4 106.7(5) . 2_655 ?
N4 Cu2 N2 101.2(4) . 2_655 ?
N4 Cu2 N2 122.8(3) 2_655 2_655 ?
N4 Cu2 N2 122.8(2) . . ?
N4 Cu2 N2 101.18(18) 2_655 . ?
N2 Cu2 N2 104.0(5) 2_655 . ?
O1 Cl3 O3 113.7(14) . . ?
O1 Cl3 O2 117.8(10) . . ?
O3 Cl3 O2 114.0(15) . . ?
O1 Cl3 O4 105.3(13) . . ?
O3 Cl3 O4 100.8(14) . . ?
O2 Cl3 O4 102.6(14) . . ?
N3 C3 C61 112.4(15) . 4_646 ?
N6 C6 C50 113.6(10) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        20.21
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.647
_refine_diff_density_min         -1.214
_refine_diff_density_rms         0.163

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.750 -0.047 0.500 441 152 ' '
2 0.250 -0.048 0.500 441 152 ' '
_platon_squeeze_details          
;
;




