# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shi_3798_ilgu
_database_code_depnum_ccdc_archive 'CCDC 1878181'
loop_
_audit_author_name
_audit_author_address
'Ilya Guralskiy'
;Taras Shevchenko National University of Kyiv
Ukraine
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-02-18 downloaded from the CCDC.
;
_audit_creation_date             2018-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Ag2 Fe N8'
_chemical_formula_sum            'C20 H12 Ag2 Fe N8'
_chemical_formula_weight         635.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20  H12  Ag2  Fe1  N8'
_chemical_oxdiff_usercomment     HV79_RT
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.4739(8)
_cell_length_b                   13.8064(7)
_cell_length_c                   20.7510(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4146.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3115
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0600
_cell_measurement_theta_min      2.0200
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.626
_exptl_absorpt_coefficient_mu    2.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_density_diffrn    2.037
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.263
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -35.00   1.00   25.00    --  -23.85-178.00  60.00   38
  2  ω      7.00  88.00   1.00   25.00    --   26.35  38.00  30.00   81
  3  ω    -29.00  50.00   1.00   25.00    --   26.35 -19.00-150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0074167000
_diffrn_orient_matrix_UB_12      -0.0239693000
_diffrn_orient_matrix_UB_13      -0.0297912000
_diffrn_orient_matrix_UB_21      0.0453184000
_diffrn_orient_matrix_UB_22      0.0194324000
_diffrn_orient_matrix_UB_23      -0.0014060000
_diffrn_orient_matrix_UB_31      0.0169978000
_diffrn_orient_matrix_UB_32      -0.0410854000
_diffrn_orient_matrix_UB_33      0.0167451000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3011
_reflns_number_total             3661
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.169
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.154
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0661
_refine_ls_restrained_S_all      1.210
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+47.1399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2)
Uanis(N1) = Uanis(N3)
3.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C5(H5), C11(H11), C12(H12), C7(H7), C9(H9), C20(H20), C8(H8),
 C17(H17), C19(H19), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Ag2 Ag 0.30563(5) 0.43843(5) 0.38879(4) 0.0364(2) Uani 1 1 d . . . . .
Ag1 Ag 0.73359(5) 1.00984(5) 0.47601(4) 0.0369(2) Uani 1 1 d . . . . .
Fe1 Fe 0.49557(8) 0.74489(8) 0.43479(5) 0.0178(3) Uani 1 1 d . . . . .
N5 N 0.5403(5) 0.7590(5) 0.3437(3) 0.0227(16) Uani 1 1 d . . . . .
N6 N 0.4511(4) 0.7278(5) 0.5258(3) 0.0214(15) Uani 1 1 d . . . . .
N3 N 0.5998(5) 0.6570(5) 0.4529(3) 0.0294(12) Uani 1 1 d . . . . .
N4 N 0.4206(5) 0.6334(5) 0.4089(3) 0.0279(17) Uani 1 1 d . . . . .
C1 C 0.3289(5) 0.8750(6) 0.4047(4) 0.0184(12) Uani 1 1 d . . . . .
N2 N 0.5745(5) 0.8525(5) 0.4596(3) 0.0286(17) Uani 1 1 d . . . . .
N7 N 0.6335(5) 0.7904(5) 0.1539(4) 0.0314(18) Uani 1 1 d . . . . .
N1 N 0.3928(5) 0.8290(5) 0.4160(3) 0.0294(12) Uani 1 1 d . . . . .
C2 C 0.6269(5) 0.9127(6) 0.4706(4) 0.0184(12) Uani 1 1 d . . . . .
C13 C 0.4238(6) 0.8006(6) 0.5624(4) 0.0252(19) Uani 1 1 d . . . . .
H13 H 0.425979 0.862824 0.545211 0.030 Uiso 1 1 calc R . . . .
C5 C 0.5596(6) 0.6823(5) 0.3079(4) 0.0242(19) Uani 1 1 d . . . . .
H5 H 0.553756 0.621528 0.326832 0.029 Uiso 1 1 calc R . . . .
C6 C 0.5885(6) 0.6864(6) 0.2432(4) 0.0237(19) Uani 1 1 d . . . . .
C11 C 0.5836(6) 0.8600(6) 0.2543(4) 0.029(2) Uani 1 1 d . . . . .
H11 H 0.591788 0.922014 0.237821 0.034 Uiso 1 1 calc R . . . .
C4 C 0.3782(6) 0.5670(6) 0.3954(4) 0.029(2) Uani 1 1 d . . . . .
C12 C 0.5534(6) 0.8480(6) 0.3155(4) 0.027(2) Uani 1 1 d . . . . .
H12 H 0.540796 0.902994 0.339856 0.032 Uiso 1 1 calc R . . . .
C7 C 0.6032(6) 0.6037(6) 0.2046(4) 0.033(2) Uani 1 1 d . . . . .
H7 H 0.594651 0.541768 0.221186 0.040 Uiso 1 1 calc R . . . .
C14 C 0.3912(6) 0.7891(7) 0.6264(4) 0.032(2) Uani 1 1 d . . . . .
C3 C 0.6598(6) 0.6055(6) 0.4628(4) 0.028(2) Uani 1 1 d . . . . .
C18 C 0.3862(6) 0.6957(8) 0.6517(4) 0.036(2) Uani 1 1 d . . . . .
C9 C 0.6454(6) 0.7109(7) 0.1199(4) 0.033(2) Uani 1 1 d . . . . .
H9 H 0.665440 0.717987 0.077587 0.040 Uiso 1 1 calc R . . . .
C20 C 0.4446(6) 0.6359(6) 0.5517(4) 0.032(2) Uani 1 1 d . . . . .
H20 H 0.462115 0.583354 0.526418 0.038 Uiso 1 1 calc R . . . .
N8 N 0.3575(6) 0.6783(8) 0.7142(4) 0.054(3) Uani 1 1 d . . . . .
C10 C 0.6024(6) 0.7796(6) 0.2161(4) 0.0224(19) Uani 1 1 d . . . . .
C8 C 0.6306(7) 0.6174(7) 0.1420(5) 0.037(2) Uani 1 1 d . . . . .
H8 H 0.639130 0.564640 0.114728 0.045 Uiso 1 1 calc R . . . .
C17 C 0.3354(7) 0.7554(10) 0.7484(5) 0.053(3) Uani 1 1 d . . . . .
H17 H 0.317022 0.745175 0.790842 0.063 Uiso 1 1 calc R . . . .
C19 C 0.4136(7) 0.6190(7) 0.6125(5) 0.040(2) Uani 1 1 d . . . . .
H19 H 0.410769 0.555937 0.628060 0.048 Uiso 1 1 calc R . . . .
C15 C 0.3649(7) 0.8696(8) 0.6649(5) 0.044(3) Uani 1 1 d . . . . .
H15 H 0.366526 0.932472 0.648820 0.052 Uiso 1 1 calc R . . . .
C16 C 0.3373(7) 0.8509(9) 0.7265(5) 0.051(3) Uani 1 1 d . . . . .
H16 H 0.319845 0.901322 0.753629 0.062 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
Ag2 Ag1 3.0771(10) 4_466 ?
Ag2 C1 2.160(8) 8_655 ?
Ag2 N7 2.396(7) 3_645 ?
Ag2 C4 2.068(8) . ?
Ag1 C2 2.049(7) . ?
Ag1 C3 2.050(8) 8_765 ?
Fe1 N5 2.008(7) . ?
Fe1 N6 2.008(7) . ?
Fe1 N3 1.973(8) . ?
Fe1 N4 1.959(7) . ?
Fe1 N2 1.944(7) . ?
Fe1 N1 1.926(8) . ?
N5 C5 1.324(10) . ?
N5 C12 1.373(10) . ?
N6 C13 1.321(10) . ?
N6 C20 1.381(10) . ?
N3 C3 1.140(10) . ?
N4 C4 1.137(10) . ?
C1 N1 1.148(10) . ?
N2 C2 1.147(10) . ?
N7 C9 1.316(11) . ?
N7 C10 1.376(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.420(12) . ?
C5 H5 0.9300 . ?
C5 C6 1.408(12) . ?
C6 C7 1.410(11) . ?
C6 C10 1.418(11) . ?
C11 H11 0.9300 . ?
C11 C12 1.353(12) . ?
C11 C10 1.391(11) . ?
C12 H12 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.372(13) . ?
C14 C18 1.394(13) . ?
C14 C15 1.421(13) . ?
C18 N8 1.384(12) . ?
C18 C19 1.392(13) . ?
C9 H9 0.9300 . ?
C9 C8 1.387(13) . ?
C20 H20 0.9300 . ?
C20 C19 1.360(12) . ?
N8 C17 1.318(14) . ?
C8 H8 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.396(16) . ?
C19 H19 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.364(14) . ?
C16 H16 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
C1 Ag2 Ag1 69.5(2) 8_655 4_466 ?
C1 Ag2 N7 92.4(3) 8_655 3_645 ?
N7 Ag2 Ag1 131.27(18) 3_645 4_466 ?
C4 Ag2 Ag1 85.0(2) . 4_466 ?
C4 Ag2 C1 142.7(3) . 8_655 ?
C4 Ag2 N7 124.8(3) . 3_645 ?
C2 Ag1 Ag2 117.2(2) . 4_566 ?
C2 Ag1 C3 169.2(3) . 8_765 ?
C3 Ag1 Ag2 73.6(3) 8_765 4_566 ?
N5 Fe1 N6 178.8(3) . . ?
N3 Fe1 N5 89.6(3) . . ?
N3 Fe1 N6 89.6(3) . . ?
N4 Fe1 N5 89.8(3) . . ?
N4 Fe1 N6 89.3(3) . . ?
N4 Fe1 N3 89.6(3) . . ?
N2 Fe1 N5 89.1(3) . . ?
N2 Fe1 N6 91.7(3) . . ?
N2 Fe1 N3 88.3(3) . . ?
N2 Fe1 N4 177.6(3) . . ?
N1 Fe1 N5 90.0(3) . . ?
N1 Fe1 N6 90.8(3) . . ?
N1 Fe1 N3 179.0(3) . . ?
N1 Fe1 N4 89.5(3) . . ?
N1 Fe1 N2 92.7(3) . . ?
C5 N5 Fe1 121.2(5) . . ?
C5 N5 C12 116.6(7) . . ?
C12 N5 Fe1 122.1(5) . . ?
C13 N6 Fe1 123.2(6) . . ?
C13 N6 C20 117.1(7) . . ?
C20 N6 Fe1 119.7(6) . . ?
C3 N3 Fe1 179.2(8) . . ?
C4 N4 Fe1 177.9(8) . . ?
N1 C1 Ag2 169.5(7) . 8_665 ?
C2 N2 Fe1 174.0(7) . . ?
C9 N7 Ag2 117.8(6) . 3_655 ?
C9 N7 C10 117.1(8) . . ?
C10 N7 Ag2 124.0(6) . 3_655 ?
C1 N1 Fe1 176.5(7) . . ?
N2 C2 Ag1 169.3(7) . . ?
N6 C13 H13 118.2 . . ?
N6 C13 C14 123.6(8) . . ?
C14 C13 H13 118.2 . . ?
N5 C5 H5 117.8 . . ?
N5 C5 C6 124.5(7) . . ?
C6 C5 H5 117.8 . . ?
C5 C6 C7 123.6(8) . . ?
C5 C6 C10 117.1(7) . . ?
C7 C6 C10 119.2(8) . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(8) . . ?
C10 C11 H11 120.0 . . ?
N4 C4 Ag2 169.1(8) . . ?
N5 C12 H12 118.2 . . ?
C11 C12 N5 123.6(8) . . ?
C11 C12 H12 118.2 . . ?
C6 C7 H7 121.0 . . ?
C8 C7 C6 118.0(8) . . ?
C8 C7 H7 121.0 . . ?
C13 C14 C15 121.9(9) . . ?
C18 C14 C13 118.2(8) . . ?
C18 C14 C15 119.9(9) . . ?
N3 C3 Ag1 177.0(8) . 8_755 ?
N8 C18 C14 121.9(10) . . ?
N8 C18 C19 120.1(9) . . ?
C19 C18 C14 118.0(8) . . ?
N7 C9 H9 117.3 . . ?
N7 C9 C8 125.4(8) . . ?
C8 C9 H9 117.3 . . ?
N6 C20 H20 118.6 . . ?
C19 C20 N6 122.7(9) . . ?
C19 C20 H20 118.6 . . ?
C17 N8 C18 116.0(10) . . ?
N7 C10 C6 121.1(7) . . ?
N7 C10 C11 120.8(8) . . ?
C11 C10 C6 118.1(7) . . ?
C7 C8 C9 119.0(9) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
N8 C17 H17 117.2 . . ?
N8 C17 C16 125.6(10) . . ?
C16 C17 H17 117.2 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(9) . . ?
C20 C19 H19 119.8 . . ?
C14 C15 H15 121.4 . . ?
C16 C15 C14 117.2(10) . . ?
C16 C15 H15 121.4 . . ?
C17 C16 H16 120.3 . . ?
C15 C16 C17 119.4(10) . . ?
C15 C16 H16 120.3 . . ?


_olex2_date_sample_data_collection 2018-07-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.238
_oxdiff_exptl_absorpt_empirical_full_min 0.853
####################################################################### 
# 
# 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_shi_3799_ilgu
_database_code_depnum_ccdc_archive 'CCDC 1878182'
loop_
_audit_author_name
_audit_author_address
'Ilya Guralskiy'
;Taras Shevchenko National University of Kyiv
Ukraine
;
_audit_update_record             
;
2018-11-09 deposited with the CCDC.	2019-02-18 downloaded from the CCDC.
;
_audit_creation_date             2018-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Ag2 Fe N8'
_chemical_formula_sum            'C20 H12 Ag2 Fe N8'
_chemical_formula_weight         635.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H12Ag2FeN8
_chemical_oxdiff_usercomment     HV79_RT
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   15.1721(15)
_cell_length_b                   14.0669(12)
_cell_length_c                   21.086(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4500.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1858
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.5300
_cell_measurement_theta_min      1.9440
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.647
_exptl_absorpt_coefficient_mu    2.383
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0820
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12322
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00  32.00   1.00   25.00    --  -24.01   0.00-120.00  125
  2  ω     -6.00  52.00   1.00   25.00    --   26.51 -77.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0444792000
_diffrn_orient_matrix_UB_12      0.0155210000
_diffrn_orient_matrix_UB_13      0.0012242000
_diffrn_orient_matrix_UB_21      -0.0031816000
_diffrn_orient_matrix_UB_22      0.0040564000
_diffrn_orient_matrix_UB_23      0.0334571000
_diffrn_orient_matrix_UB_31      0.0141703000
_diffrn_orient_matrix_UB_32      -0.0477751000
_diffrn_orient_matrix_UB_33      0.0032504000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2990
_reflns_number_total             3968
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.842
_refine_diff_density_min         -0.691
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0894
_refine_ls_restrained_S_all      1.189
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+47.2149P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1726
_refine_ls_wR_factor_ref         0.1889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C11(H11), C13(H13), C8(H8), C20(H20), C7(H7), C9(H9),
 C19(H19), C15(H15), C17(H17), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Ag2 Ag 0.29522(7) 1.05531(7) 0.60848(5) 0.0497(3) Uani 1 1 d . . . . .
Ag1 Ag 0.73493(7) 0.49005(7) 0.52814(5) 0.0561(4) Uani 1 1 d . . . . .
Fe1 Fe 0.49638(10) 0.75537(10) 0.56652(7) 0.0289(4) Uani 1 1 d . . . . .
N1 N 0.3903(7) 0.6644(6) 0.5856(5) 0.042(2) Uani 1 1 d . . . . .
N6 N 0.4485(6) 0.7766(6) 0.4693(5) 0.040(2) Uani 1 1 d . . . . .
N2 N 0.5773(7) 0.6386(7) 0.5383(5) 0.046(3) Uani 1 1 d . . . . .
N5 N 0.5437(6) 0.7367(6) 0.6642(4) 0.038(2) Uani 1 1 d . . . . .
N4 N 0.4214(7) 0.8743(7) 0.5970(5) 0.047(3) Uani 1 1 d . . . . .
N7 N 0.6307(7) 0.7033(7) 0.8512(5) 0.046(3) Uani 1 1 d . . . . .
C10 C 0.6026(7) 0.7154(8) 0.7893(6) 0.038(3) Uani 1 1 d . . . . .
C5 C 0.5605(6) 0.8117(7) 0.6997(5) 0.030(2) Uani 1 1 d . . . . .
H5 H 0.554772 0.871557 0.681442 0.036 Uiso 1 1 calc R . . . .
C6 C 0.5863(7) 0.8063(7) 0.7634(5) 0.035(3) Uani 1 1 d . . . . .
C14 C 0.3888(8) 0.7160(10) 0.3716(6) 0.048(3) Uani 1 1 d . . . . .
C12 C 0.5570(8) 0.6505(8) 0.6908(6) 0.044(3) Uani 1 1 d . . . . .
H12 H 0.545657 0.596919 0.666270 0.053 Uiso 1 1 calc R . . . .
C11 C 0.5858(9) 0.6371(7) 0.7510(5) 0.042(3) Uani 1 1 d . . . . .
H11 H 0.594315 0.575939 0.766526 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3783(9) 0.9392(8) 0.6051(6) 0.044(3) Uani 1 1 d . . . . .
C13 C 0.4224(7) 0.7070(9) 0.4337(6) 0.041(3) Uani 1 1 d . . . . .
H13 H 0.426086 0.646008 0.450492 0.049 Uiso 1 1 calc R . . . .
N8 N 0.3589(10) 0.8267(12) 0.2851(6) 0.084(4) Uani 1 1 d . . . . .
C1 C 0.3258(8) 0.6226(8) 0.5955(6) 0.045(3) Uani 1 1 d . . . . .
C8 C 0.6266(10) 0.8726(9) 0.8628(6) 0.059(4) Uani 1 1 d . . . . .
H8 H 0.634434 0.923718 0.890219 0.071 Uiso 1 1 calc R . . . .
C2 C 0.6316(9) 0.5836(9) 0.5324(6) 0.049(3) Uani 1 1 d . . . . .
C18 C 0.3868(9) 0.8081(11) 0.3458(7) 0.061(4) Uani 1 1 d . . . . .
C20 C 0.4450(9) 0.8663(9) 0.4438(7) 0.055(3) Uani 1 1 d . . . . .
H20 H 0.464847 0.917376 0.467853 0.065 Uiso 1 1 calc R . . . .
C7 C 0.6011(10) 0.8875(9) 0.8026(7) 0.057(4) Uani 1 1 d . . . . .
H7 H 0.593349 0.948721 0.786968 0.068 Uiso 1 1 calc R . . . .
C9 C 0.6412(8) 0.7808(9) 0.8838(6) 0.052(3) Uani 1 1 d . . . . .
H9 H 0.660388 0.773834 0.925409 0.062 Uiso 1 1 calc R . . . .
C19 C 0.4135(10) 0.8830(10) 0.3846(6) 0.061(4) Uani 1 1 d . . . . .
H19 H 0.409805 0.945076 0.369653 0.073 Uiso 1 1 calc R . . . .
C15 C 0.3604(11) 0.6406(12) 0.3327(8) 0.079(5) Uani 1 1 d . . . . .
H15 H 0.360179 0.578604 0.348075 0.095 Uiso 1 1 calc R . . . .
C17 C 0.3341(12) 0.7528(16) 0.2520(8) 0.087(6) Uani 1 1 d . . . . .
H17 H 0.315097 0.763525 0.210670 0.104 Uiso 1 1 calc R . . . .
C16 C 0.3336(12) 0.6588(15) 0.2737(8) 0.087(6) Uani 1 1 d . . . . .
H16 H 0.314978 0.609782 0.247374 0.105 Uiso 1 1 calc R . . . .
N3 N 0.6043(6) 0.8467(7) 0.5492(5) 0.046(3) Uani 1 1 d . . . . .
C3 C 0.6607(8) 0.8965(9) 0.5398(6) 0.046(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ag2 Ag1 3.0890(15) 4_466 ?
Ag2 N7 2.514(10) 3_656 ?
Ag2 C4 2.064(12) . ?
Ag2 C1 2.084(12) 8_665 ?
Ag1 C2 2.049(12) . ?
Ag1 C3 2.073(13) 8_755 ?
Fe1 N1 2.096(10) . ?
Fe1 N6 2.196(10) . ?
Fe1 N2 2.135(10) . ?
Fe1 N5 2.197(10) . ?
Fe1 N4 2.123(10) . ?
Fe1 N3 2.112(10) . ?
N1 C1 1.160(14) . ?
N6 C13 1.296(14) . ?
N6 C20 1.373(14) . ?
N2 C2 1.137(14) . ?
N5 C5 1.319(13) . ?
N5 C12 1.351(14) . ?
N4 C4 1.136(14) . ?
N7 C10 1.384(15) . ?
N7 C9 1.299(15) . ?
C10 C6 1.412(15) . ?
C10 C11 1.389(15) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(15) . ?
C6 C7 1.427(16) . ?
C14 C13 1.410(16) . ?
C14 C18 1.406(19) . ?
C14 C15 1.408(18) . ?
C12 H12 0.9300 . ?
C12 C11 1.355(16) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
N8 C18 1.375(18) . ?
N8 C17 1.31(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.344(18) . ?
C8 C9 1.383(17) . ?
C18 C19 1.393(19) . ?
C20 H20 0.9300 . ?
C20 C19 1.357(17) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C19 H19 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.33(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.40(2) . ?
C16 H16 0.9300 . ?
N3 C3 1.124(15) . ?

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
N7 Ag2 Ag1 128.2(2) 3_656 4_466 ?
C4 Ag2 Ag1 89.2(3) . 4_466 ?
C4 Ag2 N7 113.2(4) . 3_656 ?
C4 Ag2 C1 153.3(5) . 8_665 ?
C1 Ag2 Ag1 73.2(3) 8_665 4_466 ?
C1 Ag2 N7 93.5(4) 8_665 3_656 ?
C2 Ag1 Ag2 113.6(4) . 4_566 ?
C2 Ag1 C3 170.6(5) . 8_755 ?
C3 Ag1 Ag2 75.7(3) 8_755 4_566 ?
N1 Fe1 N6 90.5(4) . . ?
N1 Fe1 N2 91.4(4) . . ?
N1 Fe1 N5 89.9(4) . . ?
N1 Fe1 N4 90.7(4) . . ?
N1 Fe1 N3 178.8(4) . . ?
N6 Fe1 N5 179.0(3) . . ?
N2 Fe1 N6 92.0(4) . . ?
N2 Fe1 N5 88.9(4) . . ?
N4 Fe1 N6 89.9(4) . . ?
N4 Fe1 N2 177.2(4) . . ?
N4 Fe1 N5 89.2(4) . . ?
N3 Fe1 N6 90.7(4) . . ?
N3 Fe1 N2 88.5(4) . . ?
N3 Fe1 N5 88.9(4) . . ?
N3 Fe1 N4 89.3(4) . . ?
C1 N1 Fe1 172.5(10) . . ?
C13 N6 Fe1 122.6(8) . . ?
C13 N6 C20 117.1(11) . . ?
C20 N6 Fe1 120.3(8) . . ?
C2 N2 Fe1 166.0(11) . . ?
C5 N5 Fe1 120.0(7) . . ?
C5 N5 C12 117.0(10) . . ?
C12 N5 Fe1 123.1(8) . . ?
C4 N4 Fe1 171.0(10) . . ?
C10 N7 Ag2 124.0(7) . 3_646 ?
C9 N7 Ag2 117.5(8) . 3_646 ?
C9 N7 C10 115.7(10) . . ?
N7 C10 C6 122.0(10) . . ?
N7 C10 C11 120.5(10) . . ?
C11 C10 C6 117.5(11) . . ?
N5 C5 H5 118.1 . . ?
N5 C5 C6 123.7(9) . . ?
C6 C5 H5 118.1 . . ?
C10 C6 C7 118.3(11) . . ?
C5 C6 C10 117.9(10) . . ?
C5 C6 C7 123.8(10) . . ?
C13 C14 C18 116.7(12) . . ?
C13 C14 C15 125.7(13) . . ?
C15 C14 C18 117.5(13) . . ?
N5 C12 H12 117.9 . . ?
N5 C12 C11 124.2(11) . . ?
C11 C12 H12 117.9 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(10) . . ?
C12 C11 H11 120.2 . . ?
N4 C4 Ag2 173.0(11) . . ?
N6 C13 C14 125.5(12) . . ?
N6 C13 H13 117.3 . . ?
C14 C13 H13 117.3 . . ?
C17 N8 C18 115.8(15) . . ?
N1 C1 Ag2 175.5(11) . 8_655 ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(12) . . ?
C9 C8 H8 120.2 . . ?
N2 C2 Ag1 175.1(12) . . ?
N8 C18 C14 122.9(15) . . ?
N8 C18 C19 119.5(14) . . ?
C19 C18 C14 117.7(12) . . ?
N6 C20 H20 118.9 . . ?
C19 C20 N6 122.2(13) . . ?
C19 C20 H20 118.9 . . ?
C6 C7 H7 121.1 . . ?
C8 C7 C6 117.9(12) . . ?
C8 C7 H7 121.1 . . ?
N7 C9 C8 126.5(13) . . ?
N7 C9 H9 116.7 . . ?
C8 C9 H9 116.7 . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.7(13) . . ?
C20 C19 H19 119.6 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.4(17) . . ?
C16 C15 H15 120.3 . . ?
N8 C17 H17 117.3 . . ?
N8 C17 C16 125.3(16) . . ?
C16 C17 H17 117.3 . . ?
C15 C16 C17 119.1(17) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C3 N3 Fe1 178.8(10) . . ?
N3 C3 Ag1 176.6(12) . 8_765 ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.769
