# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_ig_892_0m
_database_code_depnum_ccdc_archive 'CCDC 1478973'
_audit_update_record             
;
2016-08-24 deposited with the CCDC.
2016-09-13 downloaded from the CCDC.
;
_audit_creation_date             2016-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C16 H8 Ag4 Fe2 N12), 0.5(C4 H6 N2)'
_chemical_formula_sum            'C10 H7 Ag2 Fe N7'
_chemical_formula_weight         496.82
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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      monoclinic
_space_group_IT_number           8
_space_group_name_H-M_alt        'C 1 m 1'
_space_group_name_Hall           'C -2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   6.734(4)
_cell_length_b                   12.536(6)
_cell_length_c                   9.120(5)
_cell_angle_alpha                90
_cell_angle_beta                 118.622(10)
_cell_angle_gamma                90
_cell_volume                     675.7(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    759
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.122
_cell_measurement_theta_min      2.545
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.695
_exptl_absorpt_coefficient_mu    3.927
_exptl_absorpt_correction_T_max  0.745617
_exptl_absorpt_correction_T_min  0.421829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0743 before and 0.0409 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1031 before and 0.0569 after correction.
 The Ratio of minimum to maximum transmission is 0.56.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 3192 reflections, Rint = 0.0636
 (1970 with I > 3sig(I), Rint = 0.0551)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_min         2.544
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker SMART'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.984
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                889
_reflns_number_total             995
_reflns_special_details          
;
 _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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.200
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         995
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.043
_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)+(0.0344P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0791
_refine_special_details          
;
 Refined as a 3-component twin with general and racemic twining.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.48(10) 0.1(1) 0.422(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C4) = Uanis(N4) = Uanis(N3) = Uanis(C3)
Uanis(N1) = Uanis(N2)
Uanis(C1) = Uanis(C2)
4. Others
 Fixed Sof: H6A(0.5) H6B(0.5) H6C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3)
5.b Idealised Me refined with riding coordinates:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Fe1 Fe -0.6193(4) 0.0000 -0.9180(3) 0.0073(5) Uani 1 2 d S T P . .
Ag1 Ag -0.3537(3) 0.23302(6) -0.3985(2) 0.0222(2) Uani 1 1 d . . . . .
C1 C -0.450(2) 0.1601(9) -0.6237(15) 0.0125(15) Uani 1 1 d . . . . .
N1 N -0.5117(16) 0.1070(8) -0.7414(13) 0.0106(12) Uani 1 1 d . . . . .
C2 C -0.275(2) 0.3265(9) -0.1909(15) 0.0125(15) Uani 1 1 d . . . . .
N2 N -0.2268(16) 0.3891(7) -0.0902(13) 0.0106(12) Uani 1 1 d . . . . .
N4 N -0.915(2) 0.0000 -0.9213(17) 0.0077(10) Uani 1 2 d S T P . .
C4 C -1.0186(17) 0.0914(8) -0.9229(13) 0.0077(10) Uani 1 1 d . . . . .
H4 H -0.9509 0.1575 -0.9249 0.009 Uiso 1 1 calc R . . . .
N5 N -0.402(5) 0.0000 -0.291(3) 0.056(6) Uani 1 2 d S T P . .
N3 N -0.322(2) 0.0000 -0.9141(17) 0.0077(10) Uani 1 2 d S T P . .
C3 C -0.2261(17) 0.0908(8) -0.9216(14) 0.0077(10) Uani 1 1 d . . . . .
H3 H -0.2991 0.1565 -0.9262 0.009 Uiso 1 1 calc R . . . .
C6 C -0.832(4) 0.0000 -0.502(3) 0.036(6) Uani 1 2 d S T P . .
H6A H -0.8780 -0.0716 -0.5494 0.055 Uiso 0.5 1 calc R . . A -1
H6B H -0.8615 0.0510 -0.5916 0.055 Uiso 0.5 1 calc R . . A -1
H6C H -0.9187 0.0206 -0.4454 0.055 Uiso 0.5 1 calc R . . A -1
C5 C -0.590(4) 0.0000 -0.381(3) 0.033(5) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe1 0.0057(11) 0.0098(12) 0.0077(12) 0.000 0.0042(11) 0.000
Ag1 0.0260(5) 0.0224(4) 0.0182(4) -0.0122(7) 0.0104(5) -0.0046(11)
C1 0.014(3) 0.012(4) 0.014(3) -0.006(3) 0.009(3) -0.008(3)
N1 0.006(3) 0.014(3) 0.012(3) 0.004(2) 0.004(3) 0.000(2)
C2 0.014(3) 0.012(4) 0.014(3) -0.006(3) 0.009(3) -0.008(3)
N2 0.006(3) 0.014(3) 0.012(3) 0.004(2) 0.004(3) 0.000(2)
N4 0.005(2) 0.010(3) 0.011(3) 0.000 0.006(2) 0.000
C4 0.005(2) 0.010(3) 0.011(3) 0.000 0.006(2) 0.000
N5 0.065(18) 0.057(14) 0.062(17) 0.000 0.043(15) 0.000
N3 0.005(2) 0.010(3) 0.011(3) 0.000 0.006(2) 0.000
C3 0.005(2) 0.010(3) 0.011(3) 0.000 0.006(2) 0.000
C6 0.055(16) 0.012(10) 0.023(11) 0.000 0.003(11) 0.000
C5 0.054(16) 0.034(12) 0.011(11) 0.000 0.016(13) 0.000

_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
Fe1 N1 1.950(11) . ?
Fe1 N1 1.950(11) 2 ?
Fe1 N2 1.958(11) 4_454 ?
Fe1 N2 1.958(11) 3_444 ?
Fe1 N4 1.974(12) . ?
Fe1 N3 1.984(12) . ?
Ag1 C1 2.049(12) . ?
Ag1 C2 2.069(12) . ?
C1 N1 1.157(14) . ?
C2 N2 1.130(14) . ?
N2 Fe1 1.958(11) 3_556 ?
N4 C4 1.339(12) 2 ?
N4 C4 1.339(12) . ?
C4 H4 0.9500 . ?
C4 C3 1.403(9) 1_455 ?
N5 C5 1.13(3) . ?
N3 C3 1.327(11) . ?
N3 C3 1.327(11) 2 ?
C3 C4 1.403(9) 1_655 ?
C3 H3 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 C5 1.47(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Fe1 N1 87.0(6) . 2 ?
N1 Fe1 N2 91.3(3) 2 3_444 ?
N1 Fe1 N2 91.3(3) . 4_454 ?
N1 Fe1 N2 178.2(5) . 3_444 ?
N1 Fe1 N2 178.2(5) 2 4_454 ?
N1 Fe1 N4 89.2(4) 2 . ?
N1 Fe1 N4 89.2(4) . . ?
N1 Fe1 N3 90.7(4) 2 . ?
N1 Fe1 N3 90.7(4) . . ?
N2 Fe1 N2 90.5(6) 3_444 4_454 ?
N2 Fe1 N4 90.3(4) 3_444 . ?
N2 Fe1 N4 90.3(4) 4_454 . ?
N2 Fe1 N3 89.8(4) 3_444 . ?
N2 Fe1 N3 89.8(4) 4_454 . ?
N4 Fe1 N3 179.9(7) . . ?
C1 Ag1 C2 171.7(6) . . ?
N1 C1 Ag1 170.4(11) . . ?
C1 N1 Fe1 171.1(10) . . ?
N2 C2 Ag1 169.9(10) . . ?
C2 N2 Fe1 174.9(9) . 3_556 ?
C4 N4 Fe1 121.2(6) 2 . ?
C4 N4 Fe1 121.2(6) . . ?
C4 N4 C4 117.6(12) . 2 ?
N4 C4 H4 119.6 . . ?
N4 C4 C3 120.9(9) . 1_455 ?
C3 C4 H4 119.6 1_455 . ?
C3 N3 Fe1 120.8(6) 2 . ?
C3 N3 Fe1 120.8(6) . . ?
C3 N3 C3 118.1(12) . 2 ?
C4 C3 H3 119.4 1_655 . ?
N3 C3 C4 121.2(9) . 1_655 ?
N3 C3 H3 119.4 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
N5 C5 C6 179(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
Fe1 N4 C4 C3 -178.6(8) . . . 1_455 ?
Fe1 N3 C3 C4 -178.5(8) . . . 1_655 ?
C4 N4 C4 C3 2(2) 2 . . 1_455 ?
C3 N3 C3 C4 -5(2) 2 . . 1_655 ?

_shelx_SHELXL_version_number     2014/7
_iucr_refine_instructions_details 
;

    ig_892_0m.res created by SHELXL-2014/7

TITL IG_892_0m in Cm #8
REM Inversion of 1 Component 2, Component1=1-I1-C2
CELL 0.71073 6.7337 12.5357 9.1195 90 118.6223 90
ZERR 2 0.0035 0.0063 0.0047 0 0.0104 0
LATT -7
SYMM +X,-Y,+Z
SFAC C H Ag Fe N
UNIT 20 14 4 2 14
EADP C4 N4 N3 C3
EADP N1 N2
EADP C1 C2
 
L.S. 10
PLAN  -10 0.4 -0.5
SIZE 0.01 0.02 0.1
TEMP -100
BOND $H
CONF
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\ig892t.hkl">
REM </olex2.extras>
 
WGHT    0.034400
BASF   0.10034   0.42178
FVAR       0.41529
FE1   4   -0.619341    0.000000   -0.918005    10.50000    0.00570    0.00980 =
         0.00768    0.00000    0.00421    0.00000
AG1   3   -0.353740    0.233017   -0.398537    11.00000    0.02597    0.02239 =
         0.01819   -0.01218    0.01043   -0.00455
C1    1   -0.449778    0.160140   -0.623748    11.00000    0.01370    0.01243 =
         0.01405   -0.00632    0.00873   -0.00844
N1    5   -0.511697    0.107007   -0.741375    11.00000    0.00561    0.01361 =
         0.01188    0.00383    0.00359   -0.00031
C2    1   -0.275202    0.326548   -0.190909    11.00000    0.01370    0.01243 =
         0.01405   -0.00632    0.00873   -0.00844
N2    5   -0.226803    0.389057   -0.090202    11.00000    0.00561    0.01361 =
         0.01188    0.00383    0.00359   -0.00031
N4    5   -0.914540    0.000000   -0.921295    10.50000    0.00461    0.00978 =
         0.01100    0.00000    0.00567    0.00000
C4    1   -1.018555    0.091357   -0.922866    11.00000    0.00461    0.00978 =
         0.01100    0.00000    0.00567    0.00000
AFIX  43
H4    2   -0.950923    0.157470   -0.924852    11.00000   -1.20000
AFIX   0
 
N5    5   -0.402362    0.000000   -0.290637    10.50000    0.06461    0.05665 =
         0.06217    0.00000    0.04261    0.00000
N3    5   -0.322221    0.000000   -0.914133    10.50000    0.00461    0.00978 =
         0.01100    0.00000    0.00567    0.00000
C3    1   -0.226075    0.090754   -0.921616    11.00000    0.00461    0.00978 =
         0.01100    0.00000    0.00567    0.00000
AFIX  43
H3    2   -0.299053    0.156487   -0.926210    11.00000   -1.20000
AFIX   0
 
C6    1   -0.832148    0.000000   -0.501928    10.50000    0.05537    0.01154 =
         0.02262    0.00000    0.00284    0.00000
PART -1
AFIX 133
H6A   2   -0.878021   -0.071597   -0.549428    10.50000   -1.50000
H6B   2   -0.861540    0.050958   -0.591561    10.50000   -1.50000
H6C   2   -0.918715    0.020638   -0.445398    10.50000   -1.50000
AFIX   0
PART 0
C5    1   -0.589974    0.000000   -0.381308    10.50000    0.05403    0.03356 =
         0.01136    0.00000    0.01627    0.00000
HKLF 5
 
REM  IG_892_0m in Cm #8
REM R1 =  0.0389 for     889 Fo > 4sig(Fo)  and  0.0459 for all     995 data
REM     74 parameters refined using      2 restraints
 
END  
     
WGHT      0.0344      0.0000 

REM Highest difference peak  0.958,  deepest hole -0.896,  1-sigma level  0.200
Q1    1  -0.4620  0.2465 -0.5456  11.00000  0.05    0.96
Q2    1  -0.2755  0.2535 -0.4626  11.00000  0.05    0.95
Q3    1  -0.2893  0.0000 -0.7555  10.50000  0.05    0.92
Q4    1  -0.7007  0.0000 -0.8722  10.50000  0.05    0.89
Q5    1  -0.4443  0.2391 -0.3552  11.00000  0.05    0.86
Q6    1  -0.2409  0.2497 -0.2551  11.00000  0.05    0.84
Q7    1  -0.0810  0.1055 -0.6831  11.00000  0.05    0.82
Q8    1  -0.1926  0.1833 -0.2990  11.00000  0.05    0.82
Q9    1  -0.2831  0.2061 -0.2546  11.00000  0.05    0.81
Q10   1  -0.5284  0.0000 -0.7764  10.50000  0.05    0.78

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0389 for 889 Fo > 4sig(Fo) and 0.0459 for all 995 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.96, deepest hole -0.90
  REM Mean Shift 0, Max Shift 0.000.
  
  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0459
  REM R1_gt = 0.0389
  REM wR_ref = 0.0791
  REM GOOF = 1.044
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 995
  REM Reflections_gt = 889
  REM Parameters = n/a
  REM Hole = -0.90
  REM Peak = 0.96
  REM Flack = -0.2(2)
  
  
;
_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.48(10)
2 0.1(1)
3 0.422(3)

