# 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_i4mcm
_database_code_depnum_ccdc_archive 'CCDC 1414461'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT213_i4mcm               
;
PROBLEM: Atom C1 has ADP max/min Ratio .....        5.4 prolat
RESPONSE: Unmodeled disorder in the bridging TCNQ group.
;
_vrf_PLAT250_i4mcm               
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        4.6 Note  
RESPONSE: Unmodeled disorder in the bridging TCNQ group
;
# end Validation Reply Form
_audit_creation_date             2015-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            FeTCNQ(4,4'-bpy)_aniline
_chemical_name_systematic        
"Iron(II) tetracyanoquinodimethane 4,4'-bipyridyl aniline"
_chemical_formula_moiety         '0.25(C88 H48 Fe4 N24), 2(C6 H7 N)'
_chemical_formula_sum            'C34 H26 Fe N8'
_chemical_formula_weight         602.48
_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'
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      tetragonal
_space_group_IT_number           140
_space_group_name_H-M_alt        'I 4/m c m'
_space_group_name_Hall           '-I 4 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z+1/2'
'x, -y, -z+1/2'
'y, x, -z+1/2'
'-y, -x, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'x+1/2, -y+1/2, -z+1'
'y+1/2, x+1/2, -z+1'
'-y+1/2, -x+1/2, -z+1'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z-1/2'
'-x, y, z-1/2'
'-y, -x, z-1/2'
'y, x, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'

_cell_length_a                   12.340(2)
_cell_length_b                   12.340(2)
_cell_length_c                   22.852(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3480.0(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    110
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0507 before and 0.0431 after correction. The Ratio of minimum to maximum transmission is 0.8856. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15663
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.782
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                715
_reflns_number_total             838
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.296
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         838
_refine_ls_number_restraints     59
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.272
_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)+(0.1192P)²+18.2775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid bond restraints
 Fe1, N1, C1, C2, C3, C4, N2, C5, C6, C7
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
Fe1 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim N2 \\sim C5 \\sim C6
\\sim C7: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uiso(N1A) = Uiso(C1A) = Uiso(C2A) = Uiso(C3A) = Uiso(C4A) = Uiso(C5A) =
Uiso(C6A)
4. Others
 Fixed Sof: C5(0.5) H5(0.5) C6(0.5) H6(0.5) N1A(0.25) H1AA(0.25) H1AB(0.25)
 C1A(0.25) C2A(0.25) H2A(0.25) C3A(0.25) H3A(0.25) C4A(0.25) H4A(0.25)
 C5A(0.25) H5A(0.25) C6A(0.25) H6A(0.25)
5.a Free rotating group:
 N1A(C1A,C2A,C3A,C4A,C5A,C6A)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A)
5.c X=CH2 refined with riding coordinates:
 N1A(H1AA,H1AB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.5000 0.5000 0.5000 0.0205(6) Uani 1 8 d S TU P A .
N1 N 0.6388(4) 0.6023(4) 0.5000 0.0365(12) Uani 1 2 d S TU P . .
C1 C 0.7259(4) 0.6356(4) 0.5000 0.0407(13) Uani 1 2 d S TU P . .
C2 C 0.8345(5) 0.6655(5) 0.5000 0.0533(18) Uani 1 4 d S TU P . .
C3 C 0.9187(5) 0.5813(5) 0.5000 0.067(2) Uani 1 4 d S TU P . .
C4 C 1.0291(5) 0.6078(5) 0.5000 0.075(2) Uani 1 2 d S TU P . .
H4 H 1.0500 0.6819 0.5000 0.090 Uiso 1 2 calc RS T P . .
N2 N 0.5000 0.5000 0.4041(4) 0.0392(15) Uani 1 4 d S TU P . .
C5 C 0.4767(10) 0.4112(9) 0.3742(4) 0.0502(17) Uani 0.5 1 d . U . A -1
H5 H 0.4610 0.3469 0.3953 0.060 Uiso 0.5 1 calc R . . A -1
C6 C 0.4741(10) 0.4073(9) 0.3143(5) 0.0555(18) Uani 0.5 1 d . U . A -1
H6 H 0.4549 0.3422 0.2948 0.067 Uiso 0.5 1 calc R . . A -1
C7 C 0.5000 0.5000 0.2824(5) 0.051(2) Uani 1 4 d S TU P . .
N1A N 0.255(6) 0.218(6) 0.171(2) 0.287(18) Uiso 0.25 1 d . . . B -1
H1AA H 0.2977 0.2075 0.1405 0.345 Uiso 0.25 1 calc R . . B -1
H1AB H 0.1890 0.2439 0.1653 0.345 Uiso 0.25 1 calc R . . B -1
C1A C 0.290(4) 0.192(3) 0.2267(19) 0.287(18) Uiso 0.25 1 d G . . B -1
C2A C 0.220(4) 0.202(4) 0.275(2) 0.287(18) Uiso 0.25 1 d G . . B -1
H2A H 0.1501 0.2324 0.2697 0.345 Uiso 0.25 1 calc R . . B -1
C3A C 0.254(6) 0.168(6) 0.330(2) 0.287(18) Uiso 0.25 1 d G . . B -1
H3A H 0.2054 0.1750 0.3620 0.345 Uiso 0.25 1 calc R . . B -1
C4A C 0.356(7) 0.125(6) 0.338(2) 0.287(18) Uiso 0.25 1 d G . . B -1
H4A H 0.3775 0.1010 0.3761 0.345 Uiso 0.25 1 calc R . . B -1
C5A C 0.426(5) 0.117(6) 0.291(3) 0.287(18) Uiso 0.25 1 d G . . B -1
H5A H 0.4962 0.0879 0.2963 0.345 Uiso 0.25 1 calc R . . B -1
C6A C 0.393(4) 0.151(5) 0.236(2) 0.287(18) Uiso 0.25 1 d G . . B -1
H6A H 0.4423 0.1453 0.2039 0.345 Uiso 0.25 1 calc R . . B -1


_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 2.128(4) . ?
Fe1 N1 2.128(4) 17_666 ?
Fe1 N1 2.128(4) 19_566 ?
Fe1 N1 2.128(4) 3_655 ?
Fe1 N2 2.192(8) . ?
Fe1 N2 2.192(8) 17_666 ?
N1 C1 1.151(7) . ?
C1 C2 1.390(6) . ?
C2 C1 1.390(6) 31_665 ?
C2 C3 1.469(12) . ?
C3 C4 1.401(8) 31_665 ?
C3 C4 1.401(8) . ?
C4 C4 1.374(14) 15_545 ?
C4 H4 0.9500 . ?
N2 C5 1.322(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(12) . ?
C7 C7 1.48(2) 5_655 ?
N1A H1AA 0.8800 . ?
N1A H1AB 0.8800 . ?
N1A C1A 1.3886 . ?
C1A C2A 1.3987 . ?
C1A C6A 1.3928 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3855 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3836 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3898 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3849 . ?
C6A H6A 0.9500 . ?

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 180.0 . 17_666 ?
N1 Fe1 N1 90.002(1) . 19_566 ?
N1 Fe1 N1 90.000(1) 17_666 19_566 ?
N1 Fe1 N1 89.998(1) . 3_655 ?
N1 Fe1 N1 90.000(1) 17_666 3_655 ?
N1 Fe1 N1 180.0 19_566 3_655 ?
N1 Fe1 N2 90.000(1) . . ?
N1 Fe1 N2 90.0 3_655 . ?
N1 Fe1 N2 90.000(1) 17_666 17_666 ?
N1 Fe1 N2 90.0 19_566 . ?
N1 Fe1 N2 90.000(1) 17_666 . ?
N1 Fe1 N2 90.000(1) . 17_666 ?
N1 Fe1 N2 90.0 19_566 17_666 ?
N1 Fe1 N2 90.0 3_655 17_666 ?
N2 Fe1 N2 180.0 . 17_666 ?
C1 N1 Fe1 164.5(4) . . ?
N1 C1 C2 174.5(6) . . ?
C1 C2 C1 120.8(7) 31_665 . ?
C1 C2 C3 119.6(3) 31_665 . ?
C1 C2 C3 119.6(3) . . ?
C4 C3 C2 121.5(4) . . ?
C4 C3 C2 121.5(4) 31_665 . ?
C4 C3 C4 117.0(8) 31_665 . ?
C3 C4 H4 119.3 . . ?
C4 C4 C3 121.5(4) 15_545 . ?
C4 C4 H4 119.3 15_545 . ?
C5 N2 Fe1 121.1(5) . . ?
N2 C5 H5 118.3 . . ?
N2 C5 C6 123.4(10) . . ?
C6 C5 H5 118.3 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.3(10) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 C7 121.6(6) . 5_655 ?
H1AA N1A H1AB 120.0 . . ?
C1A N1A H1AA 120.0 . . ?
C1A N1A H1AB 120.0 . . ?
N1A C1A C2A 120.8 . . ?
N1A C1A C6A 120.6 . . ?
C6A C1A C2A 118.5 . . ?
C1A C2A H2A 119.9 . . ?
C3A C2A C1A 120.2 . . ?
C3A C2A H2A 119.9 . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A C2A 121.1 . . ?
C4A C3A H3A 119.4 . . ?
C3A C4A H4A 120.6 . . ?
C3A C4A C5A 118.7 . . ?
C5A C4A H4A 120.6 . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A C4A 120.6 . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A C1A 120.7 . . ?
C5A C6A H6A 119.6 . . ?

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
Fe1 N2 C5 C6 179.1(9) . . . . ?
C1 C2 C3 C4 0.0 . . . 31_665 ?
C1 C2 C3 C4 0.0 31_665 . . . ?
C1 C2 C3 C4 180.0 . . . . ?
C1 C2 C3 C4 180.0 31_665 . . 31_665 ?
C2 C3 C4 C4 180.0 . . . 15_545 ?
C4 C3 C4 C4 0.0 31_665 . . 15_545 ?
N2 C5 C6 C7 1.8(19) . . . . ?
C5 C6 C7 C7 179.2(9) . . . 5_655 ?
N1A C1A C2A C3A 174.8 . . . . ?
N1A C1A C6A C5A -174.7 . . . . ?
C1A C2A C3A C4A 0.5 . . . . ?
C2A C1A C6A C5A 1.9 . . . . ?
C2A C3A C4A C5A 0.7 . . . . ?
C3A C4A C5A C6A -0.7 . . . . ?
C4A C5A C6A C1A -0.7 . . . . ?
C6A C1A C2A C3A -1.8 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_i4mcm
_database_code_depnum_ccdc_archive 'CCDC 1414462'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_vrf_PLAT411_i4mcm               
;
PROBLEM: Short Inter H...H Contact  H5     ..  H1A     ..       1.30 Ang.  
RESPONSE: Disordered benzene placed in idealized position
;
_vrf_PLAT112_i4mcm               
;
PROBLEM: ADDSYM Detects Additional (Pseudo) Symm. Elem...          C Check 
RESPONSE: Disorder in the molecule exhibits Pseudo symmetry
;
_vrf_PLAT230_i4mcm               
;
PROBLEM: Hirshfeld Test Diff for    N2     --  C5      ..        8.5 su    
RESPONSE: Unmodeled Disorder in the TCNQ
;
_vrf_PLAT241_i4mcm               
;
PROBLEM: High      Ueq as Compared to Neighbors for .....         C6 Check 
RESPONSE: Unmodeled Disorder in the TCNQ
;
_audit_creation_date             2015-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            FeTCNQ(4,4'-bpy)_benzene
_chemical_name_systematic        
"Iron(II) tetracyanoquinodimethane 4,4'-bipyridyl benzene"
_chemical_formula_moiety         '0.25(C120 H80 Fe4 N24), 2(C6 H6)'
_chemical_formula_sum            'C42 H32 Fe N6'
_chemical_formula_weight         676.58
_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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.1990 0.3060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0010 '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'

_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      tetragonal
_space_group_IT_number           140
_space_group_name_H-M_alt        'I 4/m c m'
_space_group_name_Hall           '-I 4 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z'
'-x, -y, z'
'y, -x, z'
'x, -y, -z+1/2'
'y, x, -z+1/2'
'-x, y, -z+1/2'
'-y, -x, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+1/2, x+1/2, -z+1'
'-x+1/2, y+1/2, -z+1'
'-y+1/2, -x+1/2, -z+1'
'-x, -y, -z'
'y, -x, -z'
'x, y, -z'
'-y, x, -z'
'-x, y, z-1/2'
'-y, -x, z-1/2'
'x, -y, z-1/2'
'y, x, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z'
'x+1/2, -y+1/2, z'
'y+1/2, x+1/2, z'

_cell_length_a                   12.3580(6)
_cell_length_b                   12.3580(6)
_cell_length_c                   22.9288(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3501.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7442
_exptl_absorpt_correction_T_min  0.5970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1363 before and 0.0676 after correction. The Ratio of minimum to maximum transmission is 0.8022. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            61089
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         18.242
_diffrn_reflns_theta_min         2.204
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 diffractometer'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.2 mm single-pinhole'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.41328
_diffrn_source                   synchrotron
_diffrn_source_type              'Station 15-ID-B'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1328
_reflns_number_total             1717
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     60
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.2258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uiso(C1A) = Uiso(C2A) = Uiso(C3A) = Uiso(C4A) = Uiso(C5A) = Uiso(C6A)
3. Others
 Fixed Sof: C1A(0.25) H1A(0.25) C2A(0.25) H2A(0.25) C3A(0.25) H3A(0.25)
 C4A(0.25) H4A(0.25) C5A(0.25) H5A(0.25) C6A(0.25) H6A(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C1A(H1A), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A),
 C6A(H6A)
4.b Fitted hexagon refined as free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.0000 0.0000 0.0000 0.0285(3) Uani 1 8 d S T P A .
N1 N 0.10078(15) 0.14069(15) 0.0000 0.0456(5) Uani 1 2 d S T P . .
C1 C 0.13498(14) 0.22685(14) 0.0000 0.0412(5) Uani 1 2 d S T P . .
N2 N 0.0000 0.0000 0.09559(18) 0.0466(8) Uani 1 4 d S T P . .
C2 C 0.16501(15) 0.33499(15) 0.0000 0.0550(9) Uani 1 4 d S T P . .
C3 C 0.08095(19) 0.41905(19) 0.0000 0.0689(13) Uani 1 4 d S T P . .
C4 C 0.1080(2) 0.5287(2) 0.0000 0.0923(16) Uani 1 2 d S T P . .
H4 H 0.1821 0.5493 0.0000 0.111 Uiso 1 2 calc RS T P . .
C5 C -0.0206(9) 0.0887(6) 0.1245(3) 0.135(2) Uani 1 1 d . . . A -1
H5 H -0.0352 0.1535 0.1037 0.162 Uiso 1 1 calc R . . A -1
C6 C -0.0218(9) 0.0904(7) 0.1873(3) 0.146(2) Uani 1 1 d . . . A -1
H6 H -0.0381 0.1557 0.2073 0.175 Uiso 1 1 calc R . . A -1
C7 C 0.0000 0.0000 0.2178(2) 0.0585(12) Uani 1 4 d S T P . .
C1A C 0.169(7) 0.186(17) 0.374(7) 0.55(2) Uiso 0.25 1 d . . . B -1
H1A H 0.1301 0.1409 0.4002 0.656 Uiso 0.25 1 calc R . . B -1
C2A C 0.221(13) 0.141(6) 0.326(10) 0.55(2) Uiso 0.25 1 d G . . B -1
H2A H 0.2172 0.0656 0.3192 0.656 Uiso 0.25 1 calc R . . B -1
C3A C 0.278(9) 0.207(19) 0.288(4) 0.55(2) Uiso 0.25 1 d G . . B -1
H3A H 0.3135 0.1767 0.2549 0.656 Uiso 0.25 1 calc R . . B -1
C4A C 0.284(7) 0.318(17) 0.298(7) 0.55(2) Uiso 0.25 1 d G . . B -1
H4A H 0.3228 0.3633 0.2717 0.656 Uiso 0.25 1 calc R . . B -1
C5A C 0.232(13) 0.363(6) 0.346(9) 0.55(2) Uiso 0.25 1 d G . . B -1
H5A H 0.2358 0.4387 0.3527 0.656 Uiso 0.25 1 calc R . . B -1
C6A C 0.175(10) 0.297(19) 0.384(3) 0.55(2) Uiso 0.25 1 d G . . B -1
H6A H 0.1394 0.3275 0.4169 0.656 Uiso 0.25 1 calc R . . B -1


_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 2.1387(19) . ?
Fe1 N1 2.1387(19) 18 ?
Fe1 N1 2.1387(19) 17 ?
Fe1 N1 2.1387(19) 2 ?
Fe1 N2 2.192(4) 17 ?
Fe1 N2 2.192(4) . ?
N1 C1 1.146(2) . ?
C1 C2 1.387(2) . ?
N2 C5 1.307(6) . ?
C2 C1 1.387(2) 30 ?
C2 C3 1.469(4) . ?
C3 C4 1.396(3) . ?
C3 C4 1.396(3) 30 ?
C4 C4 1.386(6) 14_454 ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.439(9) . ?
C6 H6 0.9500 . ?
C6 C7 1.346(8) . ?
C7 C7 1.475(10) 5 ?
C1A H1A 0.9500 . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3900 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3900 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3900 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3900 . ?
C6A H6A 0.9500 . ?

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 180.0 . 17 ?
N1 Fe1 N1 90.0 17 2 ?
N1 Fe1 N1 90.0 . 2 ?
N1 Fe1 N1 90.0 . 18 ?
N1 Fe1 N1 90.0 17 18 ?
N1 Fe1 N1 180.00(10) 18 2 ?
N1 Fe1 N2 90.0 2 . ?
N1 Fe1 N2 90.0 . . ?
N1 Fe1 N2 90.0 2 17 ?
N1 Fe1 N2 90.0 17 17 ?
N1 Fe1 N2 90.0 17 . ?
N1 Fe1 N2 90.0 18 17 ?
N1 Fe1 N2 90.0 . 17 ?
N1 Fe1 N2 90.0 18 . ?
N2 Fe1 N2 180.0 17 . ?
C1 N1 Fe1 166.04(17) . . ?
N1 C1 C2 173.9(2) . . ?
C5 N2 Fe1 120.5(3) . . ?
C1 C2 C1 121.0(2) . 30 ?
C1 C2 C3 119.48(12) 30 . ?
C1 C2 C3 119.48(12) . . ?
C4 C3 C2 121.13(14) 30 . ?
C4 C3 C2 121.13(15) . . ?
C4 C3 C4 117.7(3) 30 . ?
C3 C4 H4 119.4 . . ?
C4 C4 C3 121.13(15) 14_454 . ?
C4 C4 H4 119.4 14_454 . ?
N2 C5 H5 119.3 . . ?
N2 C5 C6 121.5(6) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.4(6) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C7 121.4(3) . 5 ?
C2A C1A H1A 119.9 . . ?
C2A C1A C6A 120.00(6) . . ?
C6A C1A H1A 120.1 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?

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 N2 C5 C6 179.6(8) . . . . ?
C1 C2 C3 C4 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . 30 ?
C1 C2 C3 C4 180.0 30 . . 30 ?
C1 C2 C3 C4 0.0 30 . . . ?
N2 C5 C6 C7 0.9(17) . . . . ?
C2 C3 C4 C4 180.0 . . . 14_454 ?
C4 C3 C4 C4 0.0 30 . . 14_454 ?
C5 C6 C7 C7 179.6(8) . . . 5 ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_i4mcm
_database_code_depnum_ccdc_archive 'CCDC 1414463'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_vrf_THETM01_i4mcm               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data collection limits
;
_vrf_PLAT220_i4mcm               
;
PROBLEM: Large Non-Solvent  C     Ueq(max)/Ueq(min) Range       10.0 Ratio 
RESPONSE: Disorder in the toluene 
;
_vrf_PLAT222_i4mcm               
;
PROBLEM: Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        8.7 Ratio 
RESPONSE: Disorder in the toluene 
;
_vrf_PLAT601_i4mcm               
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        194 Ang3  
RESPONSE: unresolved solvent molecule 
;
_audit_creation_date             2015-07-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            Fe(TCNQ)(4,4'-bpy)_toluene
_chemical_name_systematic        
"Iron(II) tetracyanoquinodimethane 4,4'-bipyridyl toluene"
_chemical_formula_moiety         '0.25(C88 H48 Fe4 N24), 2(C7 H8)'
_chemical_formula_sum            'C36 H28 Fe N6'
_chemical_formula_weight         600.49
_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 0.0000 0.0000 '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'
Fe Fe 0.1990 0.3060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0010 '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      tetragonal
_space_group_IT_number           140
_space_group_name_H-M_alt        'I 4/m c m'
_space_group_name_Hall           '-I 4 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z+1/2'
'x, -y, -z+1/2'
'y, x, -z+1/2'
'-y, -x, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'x+1/2, -y+1/2, -z+1'
'y+1/2, x+1/2, -z+1'
'-y+1/2, -x+1/2, -z+1'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z-1/2'
'-x, y, z-1/2'
'-y, -x, z-1/2'
'y, x, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'

_cell_length_a                   12.3673(3)
_cell_length_b                   12.3673(3)
_cell_length_c                   22.9031(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3503.03(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100
_cell_measurement_theta_max      13.27
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7437
_exptl_absorpt_correction_T_min  0.6740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0501 before and 0.0437 after correction.
The Ratio of minimum to maximum transmission is 0.9063.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0078
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            39663
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        13.268
_diffrn_reflns_theta_max         13.268
_diffrn_reflns_theta_min         1.704
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Bruker-Nonius APEXII CCD area detector'
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       
'Bruker-Nonius APEXII CCD area detector and D8 diffractometer'
_diffrn_measurement_device_type  'Bruker D8 diffractometer'
_diffrn_measurement_method       'omega rotation'
_diffrn_radiation_collimation    '0.2 mm single-pinhole'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.41328
_diffrn_source                   synchrotron
_diffrn_source_type              'Station 15-ID-B'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                659
_reflns_number_total             689
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.052(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     66
_refine_ls_number_reflns         689
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.202
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1097P)²+7.2465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1676
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 Fe1, N1, C1, C2, C3, C4, N2, C5, C6, C7
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
Fe1 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim N2 \\sim C5 \\sim C6
\\sim C7: within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A)
\\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C7A) \\sim Ueq:
with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1A) = Uanis(C2A) = Uanis(C3A) = Uanis(C4A) = Uanis(C5A) = Uanis(C6A) =
Uanis(C7A)
4. Others
 Fixed Sof: C5(0.5) H5(0.5) C6(0.5) H6(0.5) C1A(0.25) C2A(0.25) H2A(0.25)
 C3A(0.25) H3A(0.25) C4A(0.25) H4A(0.25) C5A(0.25) H5A(0.25) C6A(0.25)
 H6A(0.25) C7A(0.25) H7AA(0.25) H7AB(0.25) H7AC(0.25)
5.a Free rotating group:
 C1A(C2A,C3A,C4A,C5A,C6A,C7A)
5.b Me refined with riding coordinates:
 C7A(H7AA,H7AB,H7AC)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A)
;
_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 0.5000 0.5000 0.5000 0.0252(7) Uani 1 8 d S TU P A .
N1 N 0.6399(3) 0.6014(3) 0.5000 0.0387(10) Uani 1 2 d S TU P . .
C1 C 0.7271(3) 0.6351(3) 0.5000 0.0328(10) Uani 1 2 d S TU P . .
C2 C 0.8351(3) 0.6649(3) 0.5000 0.0377(13) Uani 1 4 d S TU P . .
C3 C 0.9190(3) 0.5810(3) 0.5000 0.0441(13) Uani 1 4 d S TU P . .
C4 C 1.0282(4) 0.6077(4) 0.5000 0.0533(13) Uani 1 2 d S TU P . .
H4 H 1.0488 0.6817 0.5000 0.064 Uiso 1 2 calc RS T P . .
N2 N 0.5000 0.5000 0.5957(2) 0.0443(13) Uani 1 4 d S TU P . .
C5 C 0.5241(8) 0.5873(8) 0.6255(3) 0.0649(15) Uani 0.5 1 d . U . A -1
H5 H 0.5392 0.6521 0.6048 0.078 Uiso 0.5 1 calc R . . A -1
C6 C 0.5285(9) 0.5891(8) 0.6878(3) 0.0713(17) Uani 0.5 1 d . U . A -1
H6 H 0.5514 0.6524 0.7077 0.086 Uiso 0.5 1 calc R . . A -1
C7 C 0.5000 0.5000 0.7181(3) 0.0588(18) Uani 1 4 d S TU P . .
C1A C 0.334(4) 0.339(5) 0.1515(19) 0.371(10) Uani 0.25 1 d . U . B -1
C2A C 0.385(5) 0.370(5) 0.203(2) 0.371(10) Uani 0.25 1 d G U . B -1
H2A H 0.4383 0.4252 0.2017 0.445 Uiso 0.25 1 calc R . . B -1
C3A C 0.360(6) 0.321(6) 0.2558(19) 0.371(10) Uani 0.25 1 d G U . B -1
H3A H 0.3964 0.3432 0.2904 0.445 Uiso 0.25 1 calc R . . B -1
C4A C 0.284(6) 0.240(6) 0.258(2) 0.371(10) Uani 0.25 1 d G U . B -1
H4A H 0.2672 0.2060 0.2945 0.445 Uiso 0.25 1 calc R . . B -1
C5A C 0.231(4) 0.209(5) 0.208(3) 0.371(10) Uani 0.25 1 d G U . B -1
H5A H 0.1772 0.1544 0.2094 0.445 Uiso 0.25 1 calc R . . B -1
C6A C 0.256(4) 0.258(5) 0.155(3) 0.371(10) Uani 0.25 1 d G U . B -1
H6A H 0.2185 0.2361 0.1208 0.445 Uiso 0.25 1 calc R . . B -1
C7A C 0.361(6) 0.389(6) 0.094(2) 0.371(10) Uani 0.25 1 d G U . B -1
H7AA H 0.4175 0.4439 0.0993 0.557 Uiso 0.25 1 calc R . . B -1
H7AB H 0.3878 0.3331 0.0670 0.557 Uiso 0.25 1 calc R . . B -1
H7AC H 0.2966 0.4229 0.0771 0.557 Uiso 0.25 1 calc R . . B -1


_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 2.137(4) 17_666 ?
Fe1 N1 2.137(4) 3_655 ?
Fe1 N1 2.137(4) 19_566 ?
Fe1 N1 2.137(4) . ?
Fe1 N2 2.192(6) 17_666 ?
Fe1 N2 2.192(6) . ?
N1 C1 1.156(5) . ?
C1 C2 1.386(5) . ?
C2 C1 1.386(5) 31_665 ?
C2 C3 1.468(9) . ?
C3 C4 1.389(6) 31_665 ?
C3 C4 1.389(6) . ?
C4 C4 1.391(10) 15_545 ?
C4 H4 0.9500 . ?
N2 C5 1.311(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.427(11) . ?
C6 H6 0.9500 . ?
C6 C7 1.350(9) . ?
C7 C7 1.459(16) 5_656 ?
C1A C2A 1.3926 . ?
C1A C6A 1.3907 . ?
C1A C7A 1.5027 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.3884 . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3802 . ?
C4A H4A 0.9500 . ?
C4A C5A 1.3796 . ?
C5A H5A 0.9500 . ?
C5A C6A 1.3858 . ?
C6A H6A 0.9500 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?

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 90.000(1) 17_666 19_566 ?
N1 Fe1 N1 180.0 17_666 . ?
N1 Fe1 N1 90.0 19_566 . ?
N1 Fe1 N1 180.0 19_566 3_655 ?
N1 Fe1 N1 90.000(1) 17_666 3_655 ?
N1 Fe1 N1 90.0 3_655 . ?
N1 Fe1 N2 90.0 3_655 . ?
N1 Fe1 N2 90.0 3_655 17_666 ?
N1 Fe1 N2 90.0 17_666 . ?
N1 Fe1 N2 90.0 19_566 . ?
N1 Fe1 N2 90.0 . 17_666 ?
N1 Fe1 N2 90.0 19_566 17_666 ?
N1 Fe1 N2 90.0 17_666 17_666 ?
N1 Fe1 N2 90.000(1) . . ?
N2 Fe1 N2 180.0 17_666 . ?
C1 N1 Fe1 165.2(3) . . ?
N1 C1 C2 174.3(4) . . ?
C1 C2 C1 120.9(5) . 31_665 ?
C1 C2 C3 119.6(2) . . ?
C1 C2 C3 119.6(2) 31_665 . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 C2 121.2(3) 31_665 . ?
C4 C3 C4 117.5(5) . 31_665 ?
C3 C4 C4 121.2(3) . 15_545 ?
C3 C4 H4 119.4 . . ?
C4 C4 H4 119.4 15_545 . ?
C5 N2 Fe1 121.4(4) . . ?
N2 C5 H5 118.6 . . ?
N2 C5 C6 122.8(8) . . ?
C6 C5 H5 118.6 . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.5(8) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C7 121.0(4) . 5_656 ?
C2A C1A C7A 121.8 . . ?
C6A C1A C2A 117.7 . . ?
C6A C1A C7A 120.5 . . ?
C1A C2A H2A 119.5 . . ?
C3A C2A C1A 121.1 . . ?
C3A C2A H2A 119.5 . . ?
C2A C3A H3A 119.8 . . ?
C4A C3A C2A 120.3 . . ?
C4A C3A H3A 119.8 . . ?
C3A C4A H4A 120.4 . . ?
C5A C4A C3A 119.3 . . ?
C5A C4A H4A 120.4 . . ?
C4A C5A H5A 119.8 . . ?
C4A C5A C6A 120.4 . . ?
C6A C5A H5A 119.8 . . ?
C1A C6A H6A 119.4 . . ?
C5A C6A C1A 121.2 . . ?
C5A C6A H6A 119.4 . . ?
C1A C7A H7AA 109.5 . . ?
C1A C7A H7AB 109.5 . . ?
C1A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 N2 C5 C6 -177.7(8) . . . . ?
C1 C2 C3 C4 180.0 31_665 . . 31_665 ?
C1 C2 C3 C4 0.0 31_665 . . . ?
C1 C2 C3 C4 180.0 . . . . ?
C1 C2 C3 C4 0.0 . . . 31_665 ?
C2 C3 C4 C4 180.0 . . . 15_545 ?
C4 C3 C4 C4 0.0 31_665 . . 15_545 ?
N2 C5 C6 C7 -4.6(17) . . . . ?
C5 C6 C7 C7 -177.9(8) . . . 5_656 ?
C1A C2A C3A C4A 0.1 . . . . ?
C2A C1A C6A C5A -0.8 . . . . ?
C2A C3A C4A C5A -0.8 . . . . ?
C3A C4A C5A C6A 0.8 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C6A C1A C2A C3A 0.7 . . . . ?
C7A C1A C2A C3A -178.6 . . . . ?
C7A C1A C6A C5A 178.6 . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_xuan039
_database_code_depnum_ccdc_archive 'CCDC 1414477'
_audit_update_record             
;
2015-07-22 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
_audit_creation_date             2015-01-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C18 H18 Fe N6 O2, 2(C3 H7 N O)'
_chemical_formula_sum            'C24 H32 Fe N8 O4'
_chemical_formula_weight         552.42
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Fe 0.35822 0.84933 11.76950 7.35730 3.52220 2.30450 4.76110 0.30720 15.35350
76.88050 1.03690004349
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.3351(15)
_cell_length_b                   8.8483(18)
_cell_length_c                   11.466(2)
_cell_angle_alpha                82.20(3)
_cell_angle_beta                 89.30(3)
_cell_angle_gamma                68.41(3)
_cell_volume                     685.0(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    110.15
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  0.7321
_exptl_absorpt_correction_T_min  0.6542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.3391
_exptl_crystal_description       block
_exptl_crystal_F_000             290.4656
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6240
_diffrn_reflns_theta_full        25.0763
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.50
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.9844
_diffrn_measured_fraction_theta_max 0.9844
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1924
_reflns_number_total             2396
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         2.0531
_refine_diff_density_min         -1.4995
_refine_diff_density_rms         0.1825
_refine_ls_d_res_high            0.8385
_refine_ls_d_res_low             8.1452
_refine_ls_goodness_of_fit_ref   1.0525
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0887
_refine_ls_restrained_S_all      1.0525
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1611P)²+2.9901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2517
_refine_ls_wR_factor_ref         0.2680
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C13(H13), C19(H19)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Fe1 Fe 0.0 1.0 0.0 0.0170(4) Uani 1.000000 2 S T P
O1 O 0.1049(7) 0.7418(5) 0.0326(4) 0.0277(11) Uani 1.000000 1 . . .
N1 N 0.2041(8) 0.9934(7) 0.1323(5) 0.0239(12) Uani 1.000000 1 . . .
N2 N -0.2193(8) 1.0125(7) 0.1237(5) 0.0253(12) Uani 1.000000 1 . . .
N5 N 0.2619(8) 0.4822(7) -0.0072(5) 0.0307(13) Uani 1.000000 1 . . .
C1 C 0.3335(9) 0.9942(7) 0.1869(5) 0.0211(13) Uani 1.000000 1 . . .
C2 C 0.4958(9) 0.9969(7) 0.2490(5) 0.0199(13) Uani 1.000000 1 . . .
C3 C -0.3485(9) 1.0059(7) 0.1807(5) 0.0216(14) Uani 1.000000 1 . . .
C4 C 0.4975(9) 0.9996(7) 0.3765(5) 0.0198(13) Uani 1.000000 1 . . .
C5 C 0.3626(9) 0.9579(8) 0.4468(5) 0.0216(13) Uani 1.000000 1 . . .
H5 H 0.2669(9) 0.9281(8) 0.4111(5) 0.0260(16) Uiso 1.000000 1 R . .
C6 C 0.6361(9) 1.0413(8) 0.4321(6) 0.0231(13) Uani 1.000000 1 . . .
H6 H 0.7311(9) 1.0696(8) 0.3868(6) 0.0277(16) Uiso 1.000000 1 R . .
C13 C 0.1684(9) 0.6422(8) -0.0379(6) 0.0266(15) Uani 1.000000 1 . . .
H13 H 0.1488(9) 0.6832(8) -0.1196(6) 0.0320(18) Uiso 1.000000 1 R . .
C14 C 0.3322(12) 0.3694(9) -0.0918(8) 0.044(2) Uani 1.000000 1 . . .
H14a H 0.265(6) 0.292(5) -0.083(4) 0.066(3) Uiso 1.000000 1 GR . .
H14b H 0.306(8) 0.4305(11) -0.1716(8) 0.066(3) Uiso 1.000000 1 GR . .
H14c H 0.474(2) 0.309(5) -0.078(3) 0.066(3) Uiso 1.000000 1 GR . .
C15 C 0.2880(14) 0.4142(10) 0.1172(7) 0.047(2) Uani 1.000000 1 . . .
H15a H 0.260(9) 0.5033(12) 0.1651(7) 0.071(3) Uiso 1.000000 1 GR . .
H15b H 0.198(6) 0.357(7) 0.1364(14) 0.071(3) Uiso 1.000000 1 GR . .
H15c H 0.423(3) 0.337(6) 0.1339(13) 0.071(3) Uiso 1.000000 1 GR . .
O3 O 0.2000(10) 0.6094(8) 0.6566(6) 0.0573(17) Uani 1.000000 1 . . .
N7 N 0.1639(9) 0.5998(7) 0.4604(6) 0.0380(15) Uani 1.000000 1 . . .
C19 C 0.1240(12) 0.6707(10) 0.5583(7) 0.0412(19) Uani 1.000000 1 . . .
H19 H 0.0278(12) 0.7788(10) 0.5510(7) 0.049(2) Uiso 1.000000 1 R . .
C20 C 0.3089(13) 0.4354(10) 0.4612(9) 0.050(2) Uani 1.000000 1 . . .
H20a H 0.362(7) 0.390(3) 0.5418(12) 0.076(3) Uiso 1.000000 1 GR . .
H20b H 0.247(3) 0.366(2) 0.432(5) 0.076(3) Uiso 1.000000 1 GR . .
H20c H 0.416(5) 0.4399(14) 0.410(4) 0.076(3) Uiso 1.000000 1 GR . .
C21 C 0.0616(14) 0.6854(10) 0.3506(8) 0.054(2) Uani 1.000000 1 . . .
H21a H -0.023(8) 0.797(3) 0.3611(16) 0.080(3) Uiso 1.000000 1 GR . .
H21b H 0.1569(14) 0.689(7) 0.2908(17) 0.080(3) Uiso 1.000000 1 GR . .
H21c H -0.019(8) 0.628(5) 0.325(3) 0.080(3) Uiso 1.000000 1 GR . .


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 O1 2.105(4) . ?
Fe1 O1 2.105(4) 2_575 ?
Fe1 N1 2.124(5) 2_575 ?
Fe1 N1 2.124(5) . ?
Fe1 N2 2.113(6) . ?
Fe1 N2 2.113(6) 2_575 ?
O1 C13 1.237(8) . ?
N1 C1 1.146(8) . ?
N2 C3 1.160(8) . ?
N5 C13 1.324(9) . ?
N5 C14 1.440(10) . ?
N5 C15 1.457(10) . ?
C1 C2 1.404(8) . ?
C2 C3 1.397(9) 1_655 ?
C2 C4 1.466(8) . ?
C4 C5 1.390(9) . ?
C4 C6 1.390(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(9) 2_676 ?
C6 H6 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
C15 H15a 0.9800 . ?
C15 H15b 0.9800 . ?
C15 H15c 0.9800 . ?
O3 C19 1.226(10) . ?
N7 C19 1.336(10) . ?
N7 C20 1.452(10) . ?
N7 C21 1.438(11) . ?
C19 H19 0.9500 . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O1 180.0 2_575 . ?
N1 Fe1 O1 88.4(2) . . ?
N1 Fe1 O1 91.6(2) . 2_575 ?
N1 Fe1 O1 91.6(2) 2_575 . ?
N1 Fe1 O1 88.4(2) 2_575 2_575 ?
N1 Fe1 N1 180.0 2_575 . ?
N2 Fe1 O1 89.93(19) 2_575 . ?
N2 Fe1 O1 90.07(19) 2_575 2_575 ?
N2 Fe1 O1 90.07(19) . . ?
N2 Fe1 O1 89.93(19) . 2_575 ?
N2 Fe1 N1 92.04(19) . . ?
N2 Fe1 N1 87.96(19) . 2_575 ?
N2 Fe1 N1 87.96(19) 2_575 . ?
N2 Fe1 N1 92.04(19) 2_575 2_575 ?
N2 Fe1 N2 180.0 2_575 . ?
C13 O1 Fe1 128.8(4) . . ?
C1 N1 Fe1 167.7(5) . . ?
C3 N2 Fe1 169.6(5) . 2_575 ?
C14 N5 C13 123.0(6) . . ?
C15 N5 C13 119.3(6) . . ?
C15 N5 C14 117.7(6) . . ?
C2 C1 N1 177.4(6) . . ?
C3 C2 C1 115.8(5) 1_655 . ?
C4 C2 C1 122.1(5) . . ?
C4 C2 C3 122.0(5) . 1_655 ?
C2 C3 N2 179.6(6) 1_455 . ?
C5 C4 C2 121.3(5) . . ?
C6 C4 C2 121.3(6) . . ?
C6 C4 C5 117.4(6) . . ?
H5 C5 C4 119.1(3) . . ?
C6 C5 C4 121.8(5) 2_676 . ?
C6 C5 H5 119.1(4) 2_676 . ?
C5 C6 C4 120.8(6) 2_676 . ?
H6 C6 C4 119.6(4) . . ?
H6 C6 C5 119.6(4) . 2_676 ?
N5 C13 O1 124.4(6) . . ?
H13 C13 O1 117.8(4) . . ?
H13 C13 N5 117.8(4) . . ?
H14a C14 N5 109.5 . . ?
H14b C14 N5 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 N5 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
H15a C15 N5 109.5 . . ?
H15b C15 N5 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 N5 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
C20 N7 C19 121.7(7) . . ?
C21 N7 C19 120.4(7) . . ?
C21 N7 C20 118.0(7) . . ?
N7 C19 O3 126.1(8) . . ?
H19 C19 O3 117.0(5) . . ?
H19 C19 N7 117.0(4) . . ?
H20a C20 N7 109.5 . . ?
H20b C20 N7 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 N7 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H21a C21 N7 109.5 . . ?
H21b C21 N7 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 N7 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
'Iron tetracyanoquinodimethane N,N-dimethylformamide'
_chemical_name_common            Fe(TCNQ)(DMF)2
