# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx_1
_database_code_depnum_ccdc_archive 'CCDC 2375073'
loop_
_audit_author_name
_audit_author_address
'Alessandra Crispini'
;University of Calabria
Italy
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 Ag F3 N5 O2'
_chemical_formula_sum            'C21 H17 Ag F3 N5 O2'
_chemical_formula_weight         536.27

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   25.799(5)
_cell_length_b                   12.7842(17)
_cell_length_c                   15.510(4)
_cell_angle_alpha                90
_cell_angle_beta                 122.528(14)
_cell_angle_gamma                90
_cell_volume                     4313.0(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8870
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.05

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_max          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.989
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4560
_exptl_absorpt_correction_T_max  0.7193
_exptl_absorpt_process_details   'Bruker SADABS'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_reflns_number            86714
_diffrn_reflns_av_unetI/netI     0.0083
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.634
_diffrn_reflns_theta_max         25.694
_diffrn_reflns_theta_full        25.242
_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             4112
_reflns_number_gt                3638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0335P)²+5.4097P] 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         4112
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0702
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
Ag Ag 0.45723(2) 0.32944(2) 0.34720(2) 0.06345(9) Uani 1 1 d . . . . .
N1 N 0.41394(8) 0.48074(14) 0.35336(14) 0.0457(4) Uani 1 1 d . . . . .
N2 N 0.45088(8) 0.57082(13) 0.38167(14) 0.0425(4) Uani 1 1 d . . . . .
N3 N 0.52431(8) 0.46974(15) 0.37592(13) 0.0441(4) Uani 1 1 d . . . . .
N5 N 0.39316(8) 0.01448(14) 0.25764(14) 0.0440(4) Uani 1 1 d . . . . .
N4 N 0.44064(9) 0.16580(14) 0.31461(16) 0.0481(4) Uani 1 1 d . . . . .
O1 O 0.44733(8) 0.74503(13) 0.42583(16) 0.0651(5) Uani 1 1 d . . . . .
O2 O 0.27006(8) 0.62134(18) 0.36780(17) 0.0773(6) Uani 1 1 d . . . . .
F1 F 0.33270(10) 0.84695(14) 0.37176(16) 0.0873(5) Uani 1 1 d . . . . .
F2 F 0.37994(9) 0.78533(14) 0.52558(13) 0.0813(5) Uani 1 1 d . . . . .
F3 F 0.28155(10) 0.80704(17) 0.4389(2) 0.1024(7) Uani 1 1 d . . . . .
C1 C 0.42292(10) 0.65759(16) 0.39848(17) 0.0442(5) Uani 1 1 d . . . . .
C2 C 0.36477(9) 0.61541(17) 0.37745(15) 0.0437(5) Uani 1 1 d . . . . .
C3 C 0.36380(10) 0.50784(18) 0.35054(16) 0.0453(5) Uani 1 1 d . . . . .
C4 C 0.31465(12) 0.4265(2) 0.3209(2) 0.0652(7) Uani 1 1 d . . . . .
H4A H 0.3263 0.3625 0.3033 0.098 Uiso 1 1 calc R U . . .
H4B H 0.2765 0.4509 0.2631 0.098 Uiso 1 1 calc R U . . .
H4C H 0.3099 0.4143 0.3773 0.098 Uiso 1 1 calc R U . . .
C5 C 0.31865(11) 0.66321(19) 0.38868(18) 0.0517(6) Uani 1 1 d . . . . .
C6 C 0.32866(13) 0.7769(2) 0.4318(2) 0.0618(6) Uani 1 1 d . . . . .
C7 C 0.50687(9) 0.56540(17) 0.38568(15) 0.0421(5) Uani 1 1 d . . . . .
C8 C 0.54144(12) 0.6555(2) 0.3980(2) 0.0592(6) Uani 1 1 d . . . . .
H8 H 0.5289 0.7211 0.4059 0.071 Uiso 1 1 calc R U . . .
C9 C 0.59482(12) 0.6436(2) 0.3980(2) 0.0671(7) Uani 1 1 d . . . . .
H9 H 0.6187 0.7017 0.4062 0.081 Uiso 1 1 calc R U . . .
C10 C 0.61263(11) 0.5456(2) 0.38595(19) 0.0613(7) Uani 1 1 d . . . . .
H10 H 0.6479 0.5369 0.3844 0.074 Uiso 1 1 calc R U . . .
C11 C 0.57678(11) 0.4612(2) 0.37630(17) 0.0527(5) Uani 1 1 d . . . . .
H11 H 0.5892 0.3949 0.3697 0.063 Uiso 1 1 calc R U . . .
C12 C 0.38892(10) 0.11945(17) 0.24456(17) 0.0463(5) Uani 1 1 d . . . . .
H12 H 0.3543 0.1544 0.1933 0.056 Uiso 1 1 calc R U . . .
C14 C 0.47985(11) 0.0862(2) 0.3755(2) 0.0549(6) Uani 1 1 d . . . . .
H14 H 0.5198 0.0955 0.4313 0.066 Uiso 1 1 calc R U . . .
C13 C 0.45103(10) -0.00702(19) 0.34117(19) 0.0536(6) Uani 1 1 d . . . . .
H13 H 0.4671 -0.0726 0.3685 0.064 Uiso 1 1 calc R U . . .
C15 C 0.34482(11) -0.06206(19) 0.19383(19) 0.0543(6) Uani 1 1 d . . . . .
H15A H 0.3062 -0.0373 0.1828 0.065 Uiso 1 1 calc R U . . .
H15B H 0.3546 -0.1277 0.2307 0.065 Uiso 1 1 calc R U . . .
C16 C 0.33652(9) -0.08207(15) 0.09040(17) 0.0418(5) Uani 1 1 d . . . . .
C17 C 0.28042(11) -0.1182(3) 0.0103(2) 0.0675(7) Uani 1 1 d . . . . .
H17 H 0.2481 -0.1274 0.0200 0.081 Uiso 1 1 calc R U . . .
C18 C 0.27148(14) -0.1410(3) -0.0844(2) 0.0837(9) Uani 1 1 d . . . . .
H18 H 0.2335 -0.1653 -0.1372 0.100 Uiso 1 1 calc R U . . .
C19 C 0.31823(15) -0.1280(2) -0.1006(2) 0.0695(7) Uani 1 1 d . . . . .
H19 H 0.3120 -0.1425 -0.1643 0.083 Uiso 1 1 calc R U . . .
C20 C 0.37430(15) -0.0934(2) -0.0221(2) 0.0712(8) Uani 1 1 d . . . . .
H20 H 0.4064 -0.0855 -0.0324 0.085 Uiso 1 1 calc R U . . .
C21 C 0.38376(12) -0.0699(2) 0.0735(2) 0.0618(7) Uani 1 1 d . . . . .
H21 H 0.4220 -0.0459 0.1260 0.074 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
Ag N4 2.1406(18) . ?
Ag N1 2.2612(19) . ?
Ag N3 2.3624(18) . ?
N1 C3 1.317(3) . ?
N1 N2 1.406(2) . ?
N2 C7 1.414(3) . ?
N2 C1 1.422(3) . ?
N3 C7 1.339(3) . ?
N3 C11 1.355(3) . ?
N5 C12 1.353(3) . ?
N5 C13 1.380(3) . ?
N5 C15 1.471(3) . ?
N4 C12 1.324(3) . ?
N4 C14 1.387(3) . ?
O1 C1 1.241(3) . ?
O2 C5 1.235(3) . ?
F1 C6 1.336(3) . ?
F2 C6 1.345(3) . ?
F3 C6 1.335(3) . ?
C1 C2 1.457(3) . ?
C2 C5 1.429(3) . ?
C2 C3 1.433(3) . ?
C3 C4 1.508(3) . ?
C5 C6 1.562(4) . ?
C7 C8 1.406(3) . ?
C8 C9 1.385(4) . ?
C9 C10 1.381(4) . ?
C10 C11 1.376(4) . ?
C14 C13 1.353(4) . ?
C15 C16 1.522(3) . ?
C16 C17 1.385(3) . ?
C16 C21 1.386(3) . ?
C17 C18 1.390(4) . ?
C18 C19 1.367(4) . ?
C19 C20 1.370(4) . ?
C20 C21 1.399(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
N4 Ag N1 143.64(7) . . ?
N4 Ag N3 145.05(7) . . ?
N1 Ag N3 70.79(6) . . ?
C3 N1 N2 106.48(17) . . ?
C3 N1 Ag 136.25(14) . . ?
N2 N1 Ag 116.52(13) . . ?
N1 N2 C7 118.59(17) . . ?
N1 N2 C1 111.76(16) . . ?
C7 N2 C1 129.60(17) . . ?
C7 N3 C11 117.95(19) . . ?
C7 N3 Ag 117.27(13) . . ?
C11 N3 Ag 124.63(16) . . ?
C12 N5 C13 107.34(19) . . ?
C12 N5 C15 126.0(2) . . ?
C13 N5 C15 126.7(2) . . ?
C12 N4 C14 105.95(19) . . ?
C12 N4 Ag 128.06(16) . . ?
C14 N4 Ag 125.18(16) . . ?
O1 C1 N2 123.5(2) . . ?
O1 C1 C2 133.0(2) . . ?
N2 C1 C2 103.48(17) . . ?
C5 C2 C3 124.1(2) . . ?
C5 C2 C1 129.7(2) . . ?
C3 C2 C1 105.96(19) . . ?
N1 C3 C2 112.31(18) . . ?
N1 C3 C4 118.6(2) . . ?
C2 C3 C4 129.1(2) . . ?
O2 C5 C2 125.2(2) . . ?
O2 C5 C6 115.2(2) . . ?
C2 C5 C6 119.6(2) . . ?
F3 C6 F1 106.2(2) . . ?
F3 C6 F2 107.3(2) . . ?
F1 C6 F2 107.5(2) . . ?
F3 C6 C5 110.8(2) . . ?
F1 C6 C5 112.5(2) . . ?
F2 C6 C5 112.2(2) . . ?
N3 C7 C8 122.5(2) . . ?
N3 C7 N2 115.92(18) . . ?
C8 C7 N2 121.6(2) . . ?
C9 C8 C7 117.8(2) . . ?
C10 C9 C8 120.2(2) . . ?
C11 C10 C9 118.2(2) . . ?
N3 C11 C10 123.3(2) . . ?
N4 C12 N5 110.9(2) . . ?
C13 C14 N4 109.5(2) . . ?
C14 C13 N5 106.4(2) . . ?
N5 C15 C16 114.14(18) . . ?
C17 C16 C21 117.9(2) . . ?
C17 C16 C15 119.3(2) . . ?
C21 C16 C15 122.7(2) . . ?
C16 C17 C18 121.2(3) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C20 119.3(3) . . ?
C19 C20 C21 120.7(3) . . ?
C16 C21 C20 120.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C7 -176.87(18) . . . . ?
Ag N1 N2 C7 11.5(2) . . . . ?
C3 N1 N2 C1 0.8(2) . . . . ?
Ag N1 N2 C1 -170.91(13) . . . . ?
N1 N2 C1 O1 178.7(2) . . . . ?
C7 N2 C1 O1 -4.0(4) . . . . ?
N1 N2 C1 C2 -0.6(2) . . . . ?
C7 N2 C1 C2 176.7(2) . . . . ?
O1 C1 C2 C5 -4.4(4) . . . . ?
N2 C1 C2 C5 174.8(2) . . . . ?
O1 C1 C2 C3 -179.0(3) . . . . ?
N2 C1 C2 C3 0.2(2) . . . . ?
N2 N1 C3 C2 -0.6(2) . . . . ?
Ag N1 C3 C2 168.56(16) . . . . ?
N2 N1 C3 C4 179.3(2) . . . . ?
Ag N1 C3 C4 -11.5(3) . . . . ?
C5 C2 C3 N1 -174.7(2) . . . . ?
C1 C2 C3 N1 0.3(2) . . . . ?
C5 C2 C3 C4 5.3(4) . . . . ?
C1 C2 C3 C4 -179.7(2) . . . . ?
C3 C2 C5 O2 -7.0(4) . . . . ?
C1 C2 C5 O2 179.3(2) . . . . ?
C3 C2 C5 C6 172.2(2) . . . . ?
C1 C2 C5 C6 -1.6(4) . . . . ?
O2 C5 C6 F3 0.7(3) . . . . ?
C2 C5 C6 F3 -178.6(2) . . . . ?
O2 C5 C6 F1 -118.1(3) . . . . ?
C2 C5 C6 F1 62.7(3) . . . . ?
O2 C5 C6 F2 120.6(3) . . . . ?
C2 C5 C6 F2 -58.6(3) . . . . ?
C11 N3 C7 C8 -1.2(3) . . . . ?
Ag N3 C7 C8 -176.85(18) . . . . ?
C11 N3 C7 N2 178.10(18) . . . . ?
Ag N3 C7 N2 2.4(2) . . . . ?
N1 N2 C7 N3 -9.1(3) . . . . ?
C1 N2 C7 N3 173.7(2) . . . . ?
N1 N2 C7 C8 170.2(2) . . . . ?
C1 N2 C7 C8 -7.0(3) . . . . ?
N3 C7 C8 C9 1.2(4) . . . . ?
N2 C7 C8 C9 -178.1(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 -1.4(4) . . . . ?
C7 N3 C11 C10 -0.1(3) . . . . ?
Ag N3 C11 C10 175.17(18) . . . . ?
C9 C10 C11 N3 1.4(4) . . . . ?
C14 N4 C12 N5 0.0(3) . . . . ?
Ag N4 C12 N5 -170.01(15) . . . . ?
C13 N5 C12 N4 0.1(3) . . . . ?
C15 N5 C12 N4 -179.58(19) . . . . ?
C12 N4 C14 C13 -0.1(3) . . . . ?
Ag N4 C14 C13 170.27(17) . . . . ?
N4 C14 C13 N5 0.2(3) . . . . ?
C12 N5 C13 C14 -0.2(3) . . . . ?
C15 N5 C13 C14 179.5(2) . . . . ?
C12 N5 C15 C16 75.4(3) . . . . ?
C13 N5 C15 C16 -104.2(3) . . . . ?
N5 C15 C16 C17 -155.5(2) . . . . ?
N5 C15 C16 C21 27.3(3) . . . . ?
C21 C16 C17 C18 -0.4(4) . . . . ?
C15 C16 C17 C18 -177.7(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C18 C19 C20 C21 -1.0(5) . . . . ?
C17 C16 C21 C20 0.2(4) . . . . ?
C15 C16 C21 C20 177.4(3) . . . . ?
C19 C20 C21 C16 0.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.93 2.31 2.918(3) 123.0 .
C13 H13 O1 0.93 2.64 3.452(3) 146.1 1_545
C15 H15A O2 0.97 2.63 3.485(3) 146.7 4_545
C15 H15B F1 0.97 2.56 3.162(3) 120.5 1_545

_refine_diff_density_max         0.534
_refine_diff_density_min         -0.899
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_shelx_2
_database_code_depnum_ccdc_archive 'CCDC 2375074'
loop_
_audit_author_name
_audit_author_address
'Alessandra Crispini'
;University of Calabria
Italy
;
_audit_update_record             
;
2024-08-01 deposited with the CCDC.	2024-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H19 Ag F3 N5 O2'
_chemical_formula_sum            'C18 H19 Ag F3 N5 O2'
_chemical_formula_weight         502.25

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   7.7583(10)
_cell_length_b                   11.6991(15)
_cell_length_c                   11.9243(15)
_cell_angle_alpha                104.268(6)
_cell_angle_beta                 91.117(6)
_cell_angle_gamma                102.264(6)
_cell_volume                     1022.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9660
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      24.28

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.036
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43304
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.694
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_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             4031
_reflns_number_gt                3089
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.5145P] 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         4031
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Ag Ag 0.57275(3) 0.38663(2) 0.92166(2) 0.06706(12) Uani 1 1 d . . . . .
N1 N 0.7215(3) 0.5253(2) 0.84372(19) 0.0496(6) Uani 1 1 d . . . . .
N2 N 0.8657(3) 0.6088(2) 0.91104(18) 0.0457(5) Uani 1 1 d . . . . .
N3 N 0.7728(3) 0.5373(2) 1.06970(19) 0.0516(6) Uani 1 1 d . . . . .
N4 N 0.4338(3) 0.2224(2) 0.9550(3) 0.0649(7) Uani 1 1 d . . . . .
N5 N 0.3484(5) 0.0906(3) 1.0566(3) 0.0826(9) Uani 1 1 d . . . . .
O1 O 1.1084(3) 0.7530(2) 0.88337(18) 0.0672(6) Uani 1 1 d . . . . .
O2 O 0.8527(4) 0.6146(3) 0.5299(2) 0.1002(10) Uani 1 1 d . . . . .
F1 F 1.1519(3) 0.7507(3) 0.51619(18) 0.1137(9) Uani 1 1 d . . . . .
F2 F 1.2545(3) 0.7004(2) 0.6606(2) 0.0974(7) Uani 1 1 d . . . . .
F3 F 1.1298(3) 0.8524(2) 0.6885(2) 0.0964(7) Uani 1 1 d . . . . .
C1 C 0.9734(4) 0.6745(3) 0.8436(2) 0.0491(7) Uani 1 1 d . . . . .
C2 C 0.8855(4) 0.6271(3) 0.7293(2) 0.0510(7) Uani 1 1 d . . . . .
C3 C 0.7344(4) 0.5374(3) 0.7371(2) 0.0508(7) Uani 1 1 d . . . . .
C4 C 0.5997(5) 0.4588(4) 0.6431(3) 0.0754(10) Uani 1 1 d . . . . .
H4A H 0.5246 0.3979 0.6722 0.113 Uiso 1 1 calc R U . . .
H4B H 0.6584 0.4207 0.5790 0.113 Uiso 1 1 calc R U . . .
H4C H 0.5295 0.5074 0.6176 0.113 Uiso 1 1 calc R U . . .
C5 C 0.9384(5) 0.6542(3) 0.6230(3) 0.0642(8) Uani 1 1 d . . . . .
C6 C 1.1203(5) 0.7414(4) 0.6235(3) 0.0766(10) Uani 1 1 d . . . . .
C7 C 0.8907(4) 0.6152(2) 1.0296(2) 0.0447(6) Uani 1 1 d . . . . .
C8 C 1.0303(4) 0.6973(3) 1.0996(2) 0.0595(8) Uani 1 1 d . . . . .
H8 H 1.1123 0.7502 1.0697 0.071 Uiso 1 1 calc R U . . .
C9 C 1.0431(5) 0.6977(3) 1.2155(3) 0.0707(9) Uani 1 1 d . . . . .
H9 H 1.1354 0.7516 1.2648 0.085 Uiso 1 1 calc R U . . .
C10 C 0.9211(5) 0.6193(3) 1.2587(3) 0.0681(9) Uani 1 1 d . . . . .
H10 H 0.9275 0.6199 1.3368 0.082 Uiso 1 1 calc R U . . .
C11 C 0.7906(4) 0.5407(3) 1.1829(3) 0.0610(8) Uani 1 1 d . . . . .
H11 H 0.7089 0.4861 1.2110 0.073 Uiso 1 1 calc R U . . .
C12 C 0.2980(5) 0.1311(3) 0.8939(4) 0.0927(13) Uani 1 1 d . . . . .
H12 H 0.2481 0.1265 0.8209 0.111 Uiso 1 1 calc R U . . .
C13 C 0.2487(5) 0.0504(4) 0.9552(5) 0.0980(14) Uani 1 1 d . . . . .
H13 H 0.1616 -0.0206 0.9323 0.118 Uiso 1 1 calc R U . . .
C14 C 0.4598(5) 0.1942(3) 1.0524(3) 0.0746(10) Uani 1 1 d . . . . .
H14 H 0.5450 0.2400 1.1114 0.090 Uiso 1 1 calc R U . . .
C15 C 0.3423(11) 0.0334(5) 1.1533(6) 0.159(3) Uani 1 1 d . . . . .
H15A H 0.2499 -0.0401 1.1320 0.190 Uiso 1 1 calc R U . . .
H15B H 0.4533 0.0089 1.1590 0.190 Uiso 1 1 calc R U . . .
C16 C 0.3147(8) 0.0958(5) 1.2625(5) 0.1178(17) Uani 1 1 d . . . . .
H16A H 0.2032 0.1197 1.2568 0.141 Uiso 1 1 calc R U . . .
H16B H 0.4064 0.1697 1.2834 0.141 Uiso 1 1 calc R U . . .
C17 C 0.3099(9) 0.0387(5) 1.3615(6) 0.1309(19) Uani 1 1 d . . . . .
H17A H 0.2112 -0.0311 1.3431 0.157 Uiso 1 1 calc R U . . .
H17B H 0.4164 0.0077 1.3618 0.157 Uiso 1 1 calc R U . . .
C18 C 0.2965(15) 0.1026(8) 1.4758(7) 0.243(5) Uani 1 1 d . . . . .
H18A H 0.3846 0.1771 1.4949 0.364 Uiso 1 1 calc R U . . .
H18B H 0.3147 0.0546 1.5279 0.364 Uiso 1 1 calc R U . . .
H18C H 0.1810 0.1198 1.4830 0.364 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
Ag N4 2.127(3) . ?
Ag N1 2.195(2) . ?
Ag N3 2.414(2) . ?
Ag Ag 3.2732(6) 2_667 ?
N1 C3 1.317(3) . ?
N1 N2 1.402(3) . ?
N2 C7 1.404(3) . ?
N2 C1 1.412(3) . ?
N3 C7 1.332(3) . ?
N3 C11 1.344(4) . ?
N4 C14 1.307(5) . ?
N4 C12 1.375(4) . ?
N5 C14 1.344(4) . ?
N5 C13 1.345(6) . ?
N5 C15 1.466(6) . ?
O1 C1 1.234(3) . ?
O2 C5 1.216(4) . ?
F1 C6 1.334(4) . ?
F2 C6 1.344(5) . ?
F3 C6 1.324(5) . ?
C1 C2 1.436(4) . ?
C2 C3 1.419(4) . ?
C2 C5 1.427(4) . ?
C3 C4 1.495(4) . ?
C5 C6 1.555(5) . ?
C7 C8 1.386(4) . ?
C8 C9 1.383(4) . ?
C9 C10 1.373(5) . ?
C10 C11 1.359(5) . ?
C12 C13 1.331(6) . ?
C15 C16 1.372(7) . ?
C16 C17 1.491(7) . ?
C17 C18 1.401(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
N4 Ag N1 165.28(10) . . ?
N4 Ag N3 120.85(10) . . ?
N1 Ag N3 70.95(8) . . ?
N4 Ag Ag 109.44(8) . 2_667 ?
N1 Ag Ag 83.60(6) . 2_667 ?
N3 Ag Ag 61.36(6) . 2_667 ?
C3 N1 N2 106.4(2) . . ?
C3 N1 Ag 134.60(19) . . ?
N2 N1 Ag 117.27(15) . . ?
N1 N2 C7 119.8(2) . . ?
N1 N2 C1 111.7(2) . . ?
C7 N2 C1 128.5(2) . . ?
C7 N3 C11 117.9(3) . . ?
C7 N3 Ag 114.49(17) . . ?
C11 N3 Ag 127.0(2) . . ?
C14 N4 C12 104.8(3) . . ?
C14 N4 Ag 122.4(2) . . ?
C12 N4 Ag 132.6(3) . . ?
C14 N5 C13 106.6(3) . . ?
C14 N5 C15 125.6(5) . . ?
C13 N5 C15 127.8(4) . . ?
O1 C1 N2 123.7(2) . . ?
O1 C1 C2 132.9(3) . . ?
N2 C1 C2 103.4(2) . . ?
C3 C2 C5 123.8(3) . . ?
C3 C2 C1 107.0(2) . . ?
C5 C2 C1 129.1(3) . . ?
N1 C3 C2 111.6(2) . . ?
N1 C3 C4 119.5(3) . . ?
C2 C3 C4 128.9(3) . . ?
O2 C5 C2 125.5(3) . . ?
O2 C5 C6 115.9(3) . . ?
C2 C5 C6 118.7(3) . . ?
F3 C6 F1 107.0(3) . . ?
F3 C6 F2 108.0(3) . . ?
F1 C6 F2 106.2(3) . . ?
F3 C6 C5 113.2(3) . . ?
F1 C6 C5 110.3(3) . . ?
F2 C6 C5 111.8(3) . . ?
N3 C7 C8 122.5(2) . . ?
N3 C7 N2 115.8(2) . . ?
C8 C7 N2 121.7(2) . . ?
C9 C8 C7 117.5(3) . . ?
C10 C9 C8 120.7(3) . . ?
C11 C10 C9 117.4(3) . . ?
N3 C11 C10 123.9(3) . . ?
C13 C12 N4 109.6(4) . . ?
C12 C13 N5 107.3(3) . . ?
N4 C14 N5 111.6(4) . . ?
C16 C15 N5 120.2(4) . . ?
C15 C16 C17 120.5(5) . . ?
C18 C17 C16 122.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C7 -178.4(2) . . . . ?
Ag N1 N2 C7 -11.3(3) . . . . ?
C3 N1 N2 C1 -0.6(3) . . . . ?
Ag N1 N2 C1 166.46(18) . . . . ?
N1 N2 C1 O1 -179.9(3) . . . . ?
C7 N2 C1 O1 -2.3(5) . . . . ?
N1 N2 C1 C2 0.6(3) . . . . ?
C7 N2 C1 C2 178.1(3) . . . . ?
O1 C1 C2 C3 -179.8(3) . . . . ?
N2 C1 C2 C3 -0.3(3) . . . . ?
O1 C1 C2 C5 4.3(6) . . . . ?
N2 C1 C2 C5 -176.2(3) . . . . ?
N2 N1 C3 C2 0.4(3) . . . . ?
Ag N1 C3 C2 -163.4(2) . . . . ?
N2 N1 C3 C4 179.3(3) . . . . ?
Ag N1 C3 C4 15.5(5) . . . . ?
C5 C2 C3 N1 176.1(3) . . . . ?
C1 C2 C3 N1 -0.1(4) . . . . ?
C5 C2 C3 C4 -2.7(5) . . . . ?
C1 C2 C3 C4 -178.8(3) . . . . ?
C3 C2 C5 O2 8.5(6) . . . . ?
C1 C2 C5 O2 -176.3(4) . . . . ?
C3 C2 C5 C6 -171.5(3) . . . . ?
C1 C2 C5 C6 3.7(5) . . . . ?
O2 C5 C6 F3 116.2(4) . . . . ?
C2 C5 C6 F3 -63.8(4) . . . . ?
O2 C5 C6 F1 -3.6(5) . . . . ?
C2 C5 C6 F1 176.4(3) . . . . ?
O2 C5 C6 F2 -121.5(4) . . . . ?
C2 C5 C6 F2 58.5(4) . . . . ?
C11 N3 C7 C8 0.8(4) . . . . ?
Ag N3 C7 C8 -171.2(2) . . . . ?
C11 N3 C7 N2 -179.5(3) . . . . ?
Ag N3 C7 N2 8.5(3) . . . . ?
N1 N2 C7 N3 1.0(4) . . . . ?
C1 N2 C7 N3 -176.3(3) . . . . ?
N1 N2 C7 C8 -179.2(3) . . . . ?
C1 N2 C7 C8 3.4(4) . . . . ?
N3 C7 C8 C9 -0.9(5) . . . . ?
N2 C7 C8 C9 179.4(3) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C11 1.2(6) . . . . ?
C7 N3 C11 C10 0.4(5) . . . . ?
Ag N3 C11 C10 171.2(3) . . . . ?
C9 C10 C11 N3 -1.4(5) . . . . ?
C14 N4 C12 C13 -1.0(5) . . . . ?
Ag N4 C12 C13 -176.0(3) . . . . ?
N4 C12 C13 N5 1.7(5) . . . . ?
C14 N5 C13 C12 -1.7(5) . . . . ?
C15 N5 C13 C12 179.5(4) . . . . ?
C12 N4 C14 N5 -0.1(4) . . . . ?
Ag N4 C14 N5 175.6(2) . . . . ?
C13 N5 C14 N4 1.1(5) . . . . ?
C15 N5 C14 N4 180.0(4) . . . . ?
C14 N5 C15 C16 57.6(9) . . . . ?
C13 N5 C15 C16 -123.8(7) . . . . ?
N5 C15 C16 C17 -179.5(6) . . . . ?
C15 C16 C17 C18 174.7(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O1 0.93 2.23 2.856(4) 124.0 .
C10 H10 O2 0.93 2.40 3.299(4) 163.2 1_556
C13 H13 O1 0.93 2.51 3.303(5) 143.7 1_445

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.051

