# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1499545'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Fe2 S2, 2(C12 H3 F N4)'
_chemical_formula_sum            'C46 H28 F2 Fe2 N8 S2'
_chemical_formula_weight         906.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'



loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7638(7)
_cell_length_b                   9.0088(7)
_cell_length_c                   13.4894(11)
_cell_angle_alpha                90.103(2)
_cell_angle_beta                 106.079(2)
_cell_angle_gamma                107.018(2)
_cell_volume                     974.55(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7723
_exptl_absorpt_correction_T_max  0.9147
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            7228
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         28.30
_reflns_number_total             4769
_reflns_number_gt                3880
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.2955P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4769
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1068
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.1552(4) 0.5445(4) -0.2805(3) 0.0422(10) Uani 0.493(4) 1 d . . P A 1
F2 F 0.6918(4) 0.1596(4) -0.6085(2) 0.0443(10) Uani 0.507(4) 1 d . . P A 2
C1 C 0.6933(3) 0.2803(3) -0.15088(18) 0.0263(5) Uani 1 1 d . . . . .
C2 C 0.5911(3) 0.1845(3) -0.24383(18) 0.0286(5) Uani 1 1 d . . . . .
H2 H 0.4735 0.1786 -0.2813 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6893(4) 0.1028(3) -0.27534(19) 0.0352(6) Uani 1 1 d . . . . .
H3 H 0.6527 0.0301 -0.3394 0.042 Uiso 1 1 calc R U . . .
C4 C 0.8477(4) 0.1438(3) -0.2013(2) 0.0389(6) Uani 1 1 d . . . . .
H4 H 0.9425 0.1049 -0.2039 0.047 Uiso 1 1 calc R U . . .
C5 C 0.8503(3) 0.2511(3) -0.1231(2) 0.0329(5) Uani 1 1 d . . . . .
H5 H 0.9464 0.2998 -0.0607 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5377(3) -0.0446(3) -0.02471(17) 0.0253(5) Uani 1 1 d . . . . .
C7 C 0.4597(3) -0.1364(3) -0.12273(19) 0.0320(5) Uani 1 1 d . . . . .
H7 H 0.3420 -0.1544 -0.1662 0.038 Uiso 1 1 calc R U . . .
C8 C 0.5774(4) -0.1985(3) -0.1464(2) 0.0384(6) Uani 1 1 d . . . . .
H8 H 0.5569 -0.2686 -0.2093 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7292(4) -0.1446(3) -0.0657(2) 0.0394(6) Uani 1 1 d . . . . .
H9 H 0.8339 -0.1708 -0.0617 0.047 Uiso 1 1 calc R U . . .
C10 C 0.7067(3) -0.0465(3) 0.00868(19) 0.0312(5) Uani 1 1 d . . . . .
H10 H 0.7927 0.0079 0.0741 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4301(3) 0.3798(3) -0.1397(2) 0.0387(6) Uani 1 1 d . . . . .
H11A H 0.4134 0.4033 -0.2121 0.058 Uiso 1 1 calc R U . . .
H11B H 0.3896 0.4479 -0.1037 0.058 Uiso 1 1 calc R U . . .
H11C H 0.3682 0.2707 -0.1370 0.058 Uiso 1 1 calc R U . . .
C12 C 0.9751(3) 0.2498(2) -0.50122(17) 0.0231(4) Uani 1 1 d . . . . .
C13 C 1.0919(3) 0.3520(3) -0.41421(18) 0.0256(5) Uani 1 1 d . . . . .
H13 H 1.2065 0.3584 -0.3967 0.031 Uiso 1 1 calc R U . . .
C14 C 1.0401(3) 0.4395(3) -0.35681(18) 0.0271(5) Uani 1 1 d . . . . .
H14 H 1.1203 0.5063 -0.2996 0.032 Uiso 0.507(4) 1 calc R U P A 2
C15 C 0.8705(3) 0.4357(3) -0.37859(17) 0.0226(4) Uani 1 1 d . . . . .
C16 C 0.7532(3) 0.3322(3) -0.46523(17) 0.0244(5) Uani 1 1 d . . . . .
H16 H 0.6384 0.3248 -0.4823 0.029 Uiso 1 1 calc R U . . .
C17 C 0.8056(3) 0.2454(3) -0.52257(17) 0.0246(5) Uani 1 1 d . . . . .
H17 H 0.7254 0.1784 -0.5798 0.030 Uiso 0.493(4) 1 calc R U P A 1
C18 C 1.0301(3) 0.1592(3) -0.55929(18) 0.0257(5) Uani 1 1 d . . . . .
C19 C 0.8182(3) 0.5276(3) -0.31950(18) 0.0253(5) Uani 1 1 d . . . . .
C20 C 0.9210(3) 0.0539(3) -0.64732(19) 0.0290(5) Uani 1 1 d . . . . .
C21 C 1.1988(3) 0.1582(3) -0.53251(19) 0.0290(5) Uani 1 1 d . . . . .
C22 C 0.9273(3) 0.6276(3) -0.2298(2) 0.0328(6) Uani 1 1 d . . . . .
C23 C 0.6485(3) 0.5248(3) -0.34403(18) 0.0273(5) Uani 1 1 d . . . . .
Fe1 Fe 0.66562(4) 0.04129(4) -0.13323(2) 0.02400(11) Uani 1 1 d . . . . .
N1 N 0.8401(3) -0.0321(3) -0.71736(18) 0.0414(5) Uani 1 1 d . . . . .
N2 N 1.3329(3) 0.1542(3) -0.51181(19) 0.0411(5) Uani 1 1 d . . . . .
N3 N 1.0096(3) 0.7084(3) -0.1576(2) 0.0546(7) Uani 1 1 d . . . . .
N4 N 0.5116(3) 0.5239(3) -0.36323(17) 0.0375(5) Uani 1 1 d . . . . .
S1 S 0.64787(9) 0.41183(7) -0.07807(5) 0.03546(17) 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
F1 C14 1.354(4) . ?
F2 C17 1.356(4) . ?
C1 C5 1.425(4) . ?
C1 C2 1.428(3) . ?
C1 S1 1.737(2) . ?
C1 Fe1 2.116(2) . ?
C2 C3 1.426(4) . ?
C2 Fe1 2.068(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.412(4) . ?
C3 Fe1 2.045(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.420(4) . ?
C4 Fe1 2.049(2) . ?
C4 H4 1.0000 . ?
C5 Fe1 2.073(2) . ?
C5 H5 1.0000 . ?
C6 C10 1.429(4) . ?
C6 C7 1.436(3) . ?
C6 Fe1 2.098(2) . ?
C7 C8 1.413(4) . ?
C7 Fe1 2.071(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.417(4) . ?
C8 Fe1 2.059(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.427(4) . ?
C9 Fe1 2.052(3) . ?
C9 H9 1.0000 . ?
C10 Fe1 2.052(2) . ?
C10 H10 1.0000 . ?
C11 S1 1.794(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.396(3) . ?
C12 C17 1.422(3) . ?
C12 C13 1.432(3) . ?
C13 C14 1.352(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.424(3) . ?
C14 H14 0.9500 . ?
C15 C19 1.397(3) . ?
C15 C16 1.435(3) . ?
C16 C17 1.351(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C21 1.425(3) . ?
C18 C20 1.434(3) . ?
C19 C23 1.425(3) . ?
C19 C22 1.428(3) . ?
C20 N1 1.140(3) . ?
C21 N2 1.141(3) . ?
C22 N3 1.141(4) . ?
C23 N4 1.152(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
C5 C1 C2 107.9(2) . . ?
C5 C1 S1 122.57(19) . . ?
C2 C1 S1 129.5(2) . . ?
C5 C1 Fe1 68.48(14) . . ?
C2 C1 Fe1 68.21(13) . . ?
S1 C1 Fe1 128.56(12) . . ?
C3 C2 C1 107.5(2) . . ?
C3 C2 Fe1 68.85(14) . . ?
C1 C2 Fe1 71.89(14) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.2(2) . . ?
C4 C3 Fe1 69.98(14) . . ?
C2 C3 Fe1 70.57(13) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C3 C4 C5 108.4(2) . . ?
C3 C4 Fe1 69.68(14) . . ?
C5 C4 Fe1 70.75(14) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 107.8(2) . . ?
C4 C5 Fe1 68.94(15) . . ?
C1 C5 Fe1 71.78(13) . . ?
C4 C5 H5 126.1 . . ?
C1 C5 H5 126.1 . . ?
Fe1 C5 H5 126.1 . . ?
C10 C6 C7 107.3(2) . . ?
C10 C6 Fe1 68.13(13) . . ?
C7 C6 Fe1 68.85(13) . . ?
C8 C7 C6 108.1(2) . . ?
C8 C7 Fe1 69.52(15) . . ?
C6 C7 Fe1 70.85(13) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
Fe1 C7 H7 125.9 . . ?
C7 C8 C9 108.4(2) . . ?
C7 C8 Fe1 70.45(14) . . ?
C9 C8 Fe1 69.59(15) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 125.8 . . ?
C8 C9 C10 108.2(2) . . ?
C8 C9 Fe1 70.11(15) . . ?
C10 C9 Fe1 69.63(14) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe1 C9 H9 125.9 . . ?
C9 C10 C6 107.9(2) . . ?
C9 C10 Fe1 69.67(15) . . ?
C6 C10 Fe1 71.61(14) . . ?
C9 C10 H10 126.0 . . ?
C6 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C12 C17 123.3(2) . . ?
C18 C12 C13 119.9(2) . . ?
C17 C12 C13 116.8(2) . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 F1 119.1(2) . . ?
C13 C14 C15 122.7(2) . . ?
F1 C14 C15 118.0(2) . . ?
C13 C14 H14 118.7 . . ?
F1 C14 H14 4.9 . . ?
C15 C14 H14 118.7 . . ?
C19 C15 C14 122.3(2) . . ?
C19 C15 C16 120.9(2) . . ?
C14 C15 C16 116.8(2) . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 F2 117.7(2) . . ?
C16 C17 C12 122.9(2) . . ?
F2 C17 C12 119.2(2) . . ?
C16 C17 H17 118.5 . . ?
F2 C17 H17 4.4 . . ?
C12 C17 H17 118.5 . . ?
C12 C18 C21 122.3(2) . . ?
C12 C18 C20 123.2(2) . . ?
C21 C18 C20 114.4(2) . . ?
C15 C19 C23 121.5(2) . . ?
C15 C19 C22 123.5(2) . . ?
C23 C19 C22 115.0(2) . . ?
N1 C20 C18 176.9(3) . . ?
N2 C21 C18 178.4(3) . . ?
N3 C22 C19 177.6(3) . . ?
N4 C23 C19 179.2(3) . . ?
C3 Fe1 C4 40.34(12) . . ?
C3 Fe1 C10 160.99(11) . . ?
C4 Fe1 C10 124.85(12) . . ?
C3 Fe1 C9 123.36(11) . . ?
C4 Fe1 C9 105.56(11) . . ?
C10 Fe1 C9 40.70(10) . . ?
C3 Fe1 C8 106.09(11) . . ?
C4 Fe1 C8 117.86(11) . . ?
C10 Fe1 C8 68.14(11) . . ?
C9 Fe1 C8 40.31(12) . . ?
C3 Fe1 C2 40.58(10) . . ?
C4 Fe1 C2 67.92(11) . . ?
C10 Fe1 C2 157.14(10) . . ?
C9 Fe1 C2 161.42(11) . . ?
C8 Fe1 C2 125.85(11) . . ?
C3 Fe1 C7 119.93(11) . . ?
C4 Fe1 C7 152.92(11) . . ?
C10 Fe1 C7 68.09(11) . . ?
C9 Fe1 C7 67.66(12) . . ?
C8 Fe1 C7 40.02(11) . . ?
C2 Fe1 C7 109.73(11) . . ?
C3 Fe1 C5 67.81(11) . . ?
C4 Fe1 C5 40.31(11) . . ?
C10 Fe1 C5 108.55(11) . . ?
C9 Fe1 C5 119.36(12) . . ?
C8 Fe1 C5 152.84(11) . . ?
C2 Fe1 C5 67.71(10) . . ?
C7 Fe1 C5 165.98(10) . . ?
C3 Fe1 C6 156.04(11) . . ?
C4 Fe1 C6 163.43(11) . . ?
C10 Fe1 C6 40.26(10) . . ?
C9 Fe1 C6 67.59(10) . . ?
C8 Fe1 C6 67.43(10) . . ?
C2 Fe1 C6 123.24(10) . . ?
C7 Fe1 C6 40.29(9) . . ?
C5 Fe1 C6 128.53(10) . . ?
C3 Fe1 C1 67.16(10) . . ?
C4 Fe1 C1 66.97(10) . . ?
C10 Fe1 C1 122.84(10) . . ?
C9 Fe1 C1 155.34(12) . . ?
C8 Fe1 C1 164.25(11) . . ?
C2 Fe1 C1 39.90(9) . . ?
C7 Fe1 C1 129.63(10) . . ?
C5 Fe1 C1 39.74(10) . . ?
C6 Fe1 C1 112.56(9) . . ?
C1 S1 C11 102.20(13) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.30
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.082
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1499549'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 Fe2, 2(C12 H3 Cl N4)'
_chemical_formula_sum            'C48 H32 Cl2 Fe2 N8'
_chemical_formula_weight         903.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.654(3)
_cell_length_b                   9.112(3)
_cell_length_c                   13.738(4)
_cell_angle_alpha                89.225(5)
_cell_angle_beta                 75.034(5)
_cell_angle_gamma                73.200(5)
_cell_volume                     999.6(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    0.907
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7273
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            4231
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.1268
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3346
_reflns_number_gt                1955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1215P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3346
_refine_ls_number_parameters     290
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1437
_refine_ls_R_factor_gt           0.0783
_refine_ls_wR_factor_ref         0.2199
_refine_ls_wR_factor_gt          0.1838
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.6762(11) 0.8169(10) 1.1304(5) 0.077(3) Uani 0.339(6) 1 d P A 1
C12 C 0.547(3) 0.373(3) 0.370(2) 0.054(6) Uani 0.339(6) 1 d PU A 1
H12A H 0.5598 0.4467 0.4165 0.081 Uiso 0.339(6) 1 calc PR A 1
H12B H 0.5770 0.4030 0.3010 0.081 Uiso 0.339(6) 1 calc PR A 1
H12C H 0.6199 0.2702 0.3758 0.081 Uiso 0.339(6) 1 calc PR A 1
Cl2 Cl 1.1959(4) 0.4760(5) 0.7500(3) 0.0710(15) Uani 0.661(6) 1 d P A 2
C13 C 0.2929(16) 0.4510(14) 0.4855(9) 0.047(3) Uani 0.661(6) 1 d PU A 2
H13A H 0.3515 0.5101 0.5136 0.070 Uiso 0.661(6) 1 calc PR A 2
H13B H 0.2623 0.3771 0.5336 0.070 Uiso 0.661(6) 1 calc PR A 2
H13C H 0.1914 0.5210 0.4729 0.070 Uiso 0.661(6) 1 calc PR A 2
C11 C 0.3996(12) 0.3708(9) 0.3932(7) 0.053(2) Uani 1 1 d U . .
H11A H 0.3321 0.4786 0.3917 0.064 Uiso 0.339(6) 1 calc PR A 1
H11B H 0.3748 0.3465 0.4650 0.064 Uiso 0.339(6) 1 calc PR A 1
H11C H 0.5024 0.3023 0.4070 0.064 Uiso 0.661(6) 1 d PR A 2
H11D H 0.4332 0.4458 0.3458 0.064 Uiso 0.661(6) 1 d PR A 2
C1 C 0.3238(11) 0.2755(8) 0.3426(6) 0.042(2) Uani 1 1 d . A .
C2 C 0.4065(12) 0.1799(9) 0.2538(7) 0.050(2) Uani 1 1 d . . .
H2 H 0.5251 0.1645 0.2143 0.060 Uiso 1 1 calc R A .
C3 C 0.2959(13) 0.1077(9) 0.2305(7) 0.052(2) Uani 1 1 d . A .
H3 H 0.3196 0.0366 0.1701 0.063 Uiso 1 1 calc R . .
C4 C 0.1430(12) 0.1602(9) 0.3055(7) 0.051(2) Uani 1 1 d . . .
H4 H 0.0386 0.1323 0.3076 0.062 Uiso 1 1 calc R A .
C5 C 0.1600(11) 0.2640(9) 0.3762(7) 0.047(2) Uani 1 1 d . A .
H5 H 0.0714 0.3201 0.4369 0.056 Uiso 1 1 calc R . .
C6 C 0.4574(10) -0.0412(7) 0.4776(6) 0.0332(18) Uani 1 1 d . . .
C7 C 0.5279(10) -0.1339(8) 0.3842(6) 0.0358(18) Uani 1 1 d . A .
H7 H 0.6458 -0.1564 0.3416 0.043 Uiso 1 1 calc R . .
C8 C 0.4032(10) -0.1890(8) 0.3637(6) 0.040(2) Uani 1 1 d . . .
H8 H 0.4177 -0.2589 0.3044 0.048 Uiso 1 1 calc R A .
C9 C 0.2535(10) -0.1297(9) 0.4417(6) 0.0382(19) Uani 1 1 d U A .
H9 H 0.1447 -0.1515 0.4480 0.046 Uiso 1 1 calc R . .
C10 C 0.2878(10) -0.0389(8) 0.5094(6) 0.0370(18) Uani 1 1 d . A .
H10 H 0.2050 0.0181 0.5719 0.044 Uiso 1 1 calc R . .
C14 C 0.8841(10) 0.5660(8) 0.8749(5) 0.0337(17) Uani 1 1 d . . .
C15 C 0.7680(11) 0.6556(9) 0.9638(6) 0.0404(19) Uani 1 1 d . A .
H15 H 0.6552 0.6530 0.9823 0.049 Uiso 1 1 calc R . .
C16 C 0.8176(10) 0.7429(9) 1.0210(6) 0.0396(19) Uani 1 1 d . . .
H16 H 0.7384 0.8007 1.0789 0.047 Uiso 0.661(6) 1 calc PR A 2
C17 C 0.9840(10) 0.7508(8) 0.9973(6) 0.0355(18) Uani 1 1 d . A .
C18 C 1.0989(10) 0.6623(8) 0.9113(6) 0.0410(19) Uani 1 1 d . . .
H18 H 1.2124 0.6627 0.8943 0.049 Uiso 1 1 calc R A .
C19 C 1.0484(10) 0.5756(9) 0.8518(6) 0.042(2) Uani 1 1 d . A .
H19 H 1.1275 0.5202 0.7930 0.051 Uiso 0.339(6) 1 calc PR A 1
C20 C 0.8265(10) 0.4743(8) 0.8185(6) 0.0385(19) Uani 1 1 d . . .
C21 C 1.0399(11) 0.8395(8) 1.0576(6) 0.0387(19) Uani 1 1 d . . .
C22 C 0.9247(11) 0.3803(10) 0.7282(7) 0.051(2) Uani 1 1 d . . .
C23 C 0.6575(13) 0.4723(10) 0.8465(6) 0.050(2) Uani 1 1 d . . .
C24 C 0.9360(12) 0.9318(9) 1.1463(6) 0.045(2) Uani 1 1 d . A .
C25 C 1.2077(12) 0.8468(9) 1.0290(7) 0.047(2) Uani 1 1 d . A .
Fe1 Fe 0.32617(14) 0.04585(12) 0.36970(8) 0.0302(4) Uani 1 1 d . A .
N1 N 0.9910(13) 0.3018(10) 0.6569(8) 0.093(3) Uani 1 1 d . . .
N2 N 0.5231(12) 0.4705(10) 0.8639(7) 0.073(3) Uani 1 1 d . . .
N3 N 0.8552(12) 1.0085(10) 1.2160(6) 0.076(3) Uani 1 1 d . . .
N4 N 1.3382(11) 0.8577(9) 1.0099(7) 0.068(2) 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
Cl1 C16 1.676(10) . ?
C12 C11 1.23(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H11C 0.9195 . ?
C12 H11D 1.1445 . ?
Cl2 C19 1.689(9) . ?
C13 C11 1.423(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C11 C1 1.499(11) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C1 C5 1.407(11) . ?
C1 C2 1.406(12) . ?
C1 Fe1 2.116(7) . ?
C2 C3 1.407(12) . ?
C2 Fe1 2.092(8) . ?
C2 H2 1.0000 . ?
C3 C4 1.409(12) . ?
C3 Fe1 2.047(8) . ?
C3 H3 1.0000 . ?
C4 C5 1.427(11) . ?
C4 Fe1 2.029(7) . ?
C4 H4 1.0000 . ?
C5 Fe1 2.077(8) . ?
C5 H5 1.0000 . ?
C6 C10 1.413(10) . ?
C6 C7 1.434(10) . ?
C6 C6 1.434(14) 2_656 ?
C6 Fe1 2.105(7) . ?
C7 C8 1.404(11) . ?
C7 Fe1 2.070(7) . ?
C7 H7 1.0000 . ?
C8 C9 1.418(11) . ?
C8 Fe1 2.045(7) . ?
C8 H8 1.0000 . ?
C9 C10 1.394(10) . ?
C9 Fe1 2.037(8) . ?
C9 H9 1.0000 . ?
C10 Fe1 2.041(7) . ?
C10 H10 1.0000 . ?
C14 C19 1.403(11) . ?
C14 C20 1.416(11) . ?
C14 C15 1.445(11) . ?
C15 C16 1.350(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.415(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.411(11) . ?
C17 C21 1.423(10) . ?
C18 C19 1.372(11) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C23 1.418(13) . ?
C20 C22 1.434(12) . ?
C21 C25 1.424(12) . ?
C21 C24 1.423(11) . ?
C22 N1 1.136(11) . ?
C23 N2 1.131(11) . ?
C24 N3 1.134(11) . ?
C25 N4 1.125(10) . ?

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
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H11C 52.3 . . ?
H12A C12 H11C 109.6 . . ?
H12B C12 H11C 140.7 . . ?
H12C C12 H11C 60.2 . . ?
C11 C12 H11D 49.0 . . ?
H12A C12 H11D 101.1 . . ?
H12B C12 H11D 67.4 . . ?
H12C C12 H11D 148.0 . . ?
H11C C12 H11D 100.9 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C11 C13 117.3(15) . . ?
C12 C11 C1 127.5(15) . . ?
C13 C11 C1 114.6(9) . . ?
C12 C11 H11A 105.4 . . ?
C13 C11 H11A 61.4 . . ?
C1 C11 H11A 105.4 . . ?
C12 C11 H11B 105.4 . . ?
C13 C11 H11B 44.7 . . ?
C1 C11 H11B 105.4 . . ?
H11A C11 H11B 106.0 . . ?
C12 C11 H11C 47.3 . . ?
C13 C11 H11C 108.4 . . ?
C1 C11 H11C 108.3 . . ?
H11A C11 H11C 145.7 . . ?
H11B C11 H11C 70.7 . . ?
C12 C11 H11D 60.7 . . ?
C13 C11 H11D 109.1 . . ?
C1 C11 H11D 108.6 . . ?
H11A C11 H11D 54.5 . . ?
H11B C11 H11D 144.3 . . ?
H11C C11 H11D 107.6 . . ?
C5 C1 C2 108.3(8) . . ?
C5 C1 C11 126.3(8) . . ?
C2 C1 C11 125.4(8) . . ?
C5 C1 Fe1 68.9(4) . . ?
C2 C1 Fe1 69.6(4) . . ?
C11 C1 Fe1 126.5(5) . . ?
C1 C2 C3 108.9(8) . . ?
C1 C2 Fe1 71.4(5) . . ?
C3 C2 Fe1 68.4(5) . . ?
C1 C2 H2 125.5 . . ?
C3 C2 H2 125.5 . . ?
Fe1 C2 H2 125.5 . . ?
C4 C3 C2 107.1(8) . . ?
C4 C3 Fe1 69.1(4) . . ?
C2 C3 Fe1 71.8(5) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
Fe1 C3 H3 126.4 . . ?
C3 C4 C5 108.7(8) . . ?
C3 C4 Fe1 70.4(5) . . ?
C5 C4 Fe1 71.5(4) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Fe1 C4 H4 125.7 . . ?
C1 C5 C4 107.0(8) . . ?
C1 C5 Fe1 71.9(4) . . ?
C4 C5 Fe1 67.9(4) . . ?
C1 C5 H5 126.5 . . ?
C4 C5 H5 126.5 . . ?
Fe1 C5 H5 126.5 . . ?
C10 C6 C7 106.1(7) . . ?
C10 C6 C6 128.3(9) . 2_656 ?
C7 C6 C6 125.3(9) . 2_656 ?
C10 C6 Fe1 67.7(4) . . ?
C7 C6 Fe1 68.6(4) . . ?
C6 C6 Fe1 124.3(6) 2_656 . ?
C8 C7 C6 108.1(7) . . ?
C8 C7 Fe1 69.1(4) . . ?
C6 C7 Fe1 71.2(4) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
Fe1 C7 H7 125.9 . . ?
C7 C8 C9 108.5(7) . . ?
C7 C8 Fe1 71.0(4) . . ?
C9 C8 Fe1 69.4(4) . . ?
C7 C8 H8 125.8 . . ?
C9 C8 H8 125.8 . . ?
Fe1 C8 H8 125.8 . . ?
C10 C9 C8 107.2(7) . . ?
C10 C9 Fe1 70.2(4) . . ?
C8 C9 Fe1 70.0(4) . . ?
C10 C9 H9 126.4 . . ?
C8 C9 H9 126.4 . . ?
Fe1 C9 H9 126.4 . . ?
C9 C10 C6 110.0(7) . . ?
C9 C10 Fe1 69.9(4) . . ?
C6 C10 Fe1 72.5(4) . . ?
C9 C10 H10 125.0 . . ?
C6 C10 H10 125.0 . . ?
Fe1 C10 H10 125.0 . . ?
C19 C14 C20 124.8(8) . . ?
C19 C14 C15 116.5(7) . . ?
C20 C14 C15 118.7(7) . . ?
C16 C15 C14 120.9(8) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 122.0(8) . . ?
C15 C16 Cl1 114.4(7) . . ?
C17 C16 Cl1 122.9(7) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
Cl1 C16 H16 9.4 . . ?
C16 C17 C18 117.5(7) . . ?
C16 C17 C21 123.0(7) . . ?
C18 C17 C21 119.4(7) . . ?
C19 C18 C17 120.7(8) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 122.4(8) . . ?
C18 C19 Cl2 116.6(7) . . ?
C14 C19 Cl2 121.0(6) . . ?
C18 C19 H19 118.8 . . ?
C14 C19 H19 118.8 . . ?
Cl2 C19 H19 2.6 . . ?
C23 C20 C14 121.2(8) . . ?
C23 C20 C22 113.1(7) . . ?
C14 C20 C22 125.6(8) . . ?
C25 C21 C17 120.8(7) . . ?
C25 C21 C24 114.8(7) . . ?
C17 C21 C24 124.4(8) . . ?
N1 C22 C20 174.2(11) . . ?
N2 C23 C20 176.5(9) . . ?
N3 C24 C21 178.0(10) . . ?
N4 C25 C21 176.8(10) . . ?
C4 Fe1 C9 107.3(3) . . ?
C4 Fe1 C3 40.4(4) . . ?
C9 Fe1 C3 123.8(3) . . ?
C4 Fe1 C8 120.8(3) . . ?
C9 Fe1 C8 40.7(3) . . ?
C3 Fe1 C8 107.0(3) . . ?
C4 Fe1 C10 125.2(4) . . ?
C9 Fe1 C10 40.0(3) . . ?
C3 Fe1 C10 160.8(3) . . ?
C8 Fe1 C10 67.3(3) . . ?
C4 Fe1 C7 155.7(3) . . ?
C9 Fe1 C7 67.8(3) . . ?
C3 Fe1 C7 121.0(3) . . ?
C8 Fe1 C7 39.9(3) . . ?
C10 Fe1 C7 67.2(3) . . ?
C4 Fe1 C5 40.7(3) . . ?
C9 Fe1 C5 122.0(3) . . ?
C3 Fe1 C5 67.9(4) . . ?
C8 Fe1 C5 156.9(3) . . ?
C10 Fe1 C5 109.7(3) . . ?
C7 Fe1 C5 162.2(3) . . ?
C4 Fe1 C2 66.7(4) . . ?
C9 Fe1 C2 160.7(3) . . ?
C3 Fe1 C2 39.7(3) . . ?
C8 Fe1 C2 125.1(3) . . ?
C10 Fe1 C2 158.4(3) . . ?
C7 Fe1 C2 109.7(3) . . ?
C5 Fe1 C2 66.3(4) . . ?
C4 Fe1 C6 162.0(4) . . ?
C9 Fe1 C6 67.4(3) . . ?
C3 Fe1 C6 156.9(3) . . ?
C8 Fe1 C6 67.2(3) . . ?
C10 Fe1 C6 39.8(3) . . ?
C7 Fe1 C6 40.2(3) . . ?
C5 Fe1 C6 126.2(3) . . ?
C2 Fe1 C6 123.9(3) . . ?
C4 Fe1 C1 66.6(3) . . ?
C9 Fe1 C1 157.5(3) . . ?
C3 Fe1 C1 66.7(3) . . ?
C8 Fe1 C1 161.4(3) . . ?
C10 Fe1 C1 124.4(3) . . ?
C7 Fe1 C1 126.8(3) . . ?
C5 Fe1 C1 39.2(3) . . ?
C2 Fe1 C1 39.0(3) . . ?
C6 Fe1 C1 111.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.940
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 1499547'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Fe2 S2, 2(C12 H2 F2 N4)'
_chemical_formula_sum            'C46 H26 F4 Fe2 N8 S2'
_chemical_formula_weight         942.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7754(10)
_cell_length_b                   9.0556(11)
_cell_length_c                   13.2444(16)
_cell_angle_alpha                91.068(2)
_cell_angle_beta                 105.733(2)
_cell_angle_gamma                108.766(2)
_cell_volume                     952.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7990
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            6775
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         28.22
_reflns_number_total             4605
_reflns_number_gt                3751
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0768P)²+0.0127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4605
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.1172(3) 0.5523(3) 0.37585(18) 0.0168(4) Uani 1 1 d . . .
C17 C -0.0476(3) 0.5554(3) 0.35392(19) 0.0207(5) Uani 1 1 d . . .
C13 C 0.2354(3) 0.6547(3) 0.46634(19) 0.0192(5) Uani 1 1 d . . .
H13 H 0.3499 0.6607 0.4855 0.023 Uiso 1 1 calc R . .
C14 C 0.1852(3) 0.7432(3) 0.52501(19) 0.0194(5) Uani 1 1 d . . .
C21 C 0.3358(3) 0.4605(3) 0.34159(19) 0.0206(5) Uani 1 1 d . . .
C23 C -0.2008(3) 0.8416(3) 0.53240(19) 0.0218(5) Uani 1 1 d . . .
C20 C 0.0619(3) 0.3636(3) 0.2177(2) 0.0217(5) Uani 1 1 d . . .
C19 C -0.0333(3) 0.8360(3) 0.56491(19) 0.0195(5) Uani 1 1 d . . .
C22 C 0.0723(3) 0.9395(3) 0.6566(2) 0.0220(5) Uani 1 1 d . . .
C18 C 0.1659(3) 0.4562(3) 0.31473(19) 0.0187(5) Uani 1 1 d . . .
C2 C 0.4198(3) 0.8145(3) 0.2533(2) 0.0228(5) Uani 1 1 d . . .
H2 H 0.5333 0.8228 0.2862 0.027 Uiso 1 1 calc R . .
C10 C 0.3036(3) 1.0545(3) 0.00187(19) 0.0212(5) Uani 1 1 d . . .
H10 H 0.2145 1.0024 -0.0598 0.025 Uiso 1 1 calc R . .
C7 C 0.5612(3) 1.1395(3) 0.12865(19) 0.0217(5) Uani 1 1 d . . .
H7 H 0.6747 1.1542 0.1664 0.026 Uiso 1 1 calc R . .
C1 C 0.3114(3) 0.7185(3) 0.1577(2) 0.0227(5) Uani 1 1 d . . .
C15 C 0.0187(3) 0.7447(3) 0.50289(18) 0.0178(5) Uani 1 1 d . . .
C8 C 0.4541(3) 1.2056(3) 0.1614(2) 0.0255(5) Uani 1 1 d . . .
H8 H 0.4834 1.2729 0.2246 0.031 Uiso 1 1 calc R . .
C3 C 0.3278(4) 0.8953(3) 0.2905(2) 0.0272(6) Uani 1 1 d . . .
H3 H 0.3682 0.9651 0.3538 0.033 Uiso 1 1 calc R . .
C16 C -0.0981(3) 0.6448(3) 0.41212(19) 0.0201(5) Uani 1 1 d . . .
H16 H -0.2120 0.6405 0.3920 0.024 Uiso 1 1 calc R . .
C5 C 0.1564(3) 0.7476(3) 0.1338(2) 0.0246(5) Uani 1 1 d . . .
H5 H 0.0630 0.7034 0.0728 0.029 Uiso 1 1 calc R . .
C4 C 0.1651(3) 0.8540(3) 0.2169(2) 0.0278(6) Uani 1 1 d . . .
H4 H 0.0776 0.8910 0.2224 0.033 Uiso 1 1 calc R . .
C6 C 0.4693(3) 1.0470(3) 0.02929(18) 0.0182(5) Uani 1 1 d . . .
C9 C 0.2950(3) 1.1538(3) 0.0831(2) 0.0250(5) Uani 1 1 d . . .
H9 H 0.1995 1.1808 0.0847 0.030 Uiso 1 1 calc R . .
C11 C 0.5693(3) 0.6193(3) 0.1421(2) 0.0310(6) Uani 1 1 d . . .
H11A H 0.6386 0.7299 0.1477 0.046 Uiso 1 1 calc R . .
H11B H 0.6081 0.5549 0.1015 0.046 Uiso 1 1 calc R . .
H11C H 0.5790 0.5863 0.2130 0.046 Uiso 1 1 calc R . .
F1 F 0.30091(19) 0.83533(19) 0.61135(12) 0.0296(4) Uani 1 1 d . . .
F2 F -0.16512(19) 0.4586(2) 0.26940(13) 0.0346(4) Uani 1 1 d . . .
Fe1 Fe 0.34586(4) 0.96206(4) 0.14519(3) 0.01747(12) Uani 1 1 d . . .
N1 N -0.0131(3) 0.2874(3) 0.13852(19) 0.0335(6) Uani 1 1 d . . .
N2 N 0.4721(3) 0.4641(3) 0.36166(18) 0.0288(5) Uani 1 1 d . . .
N3 N 0.1492(3) 1.0250(3) 0.73210(19) 0.0308(5) Uani 1 1 d . . .
N4 N -0.3335(3) 0.8479(3) 0.50682(19) 0.0306(5) Uani 1 1 d . . .
S1 S 0.35284(9) 0.59474(8) 0.07622(5) 0.02850(17) 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
C12 C17 1.405(3) . ?
C12 C18 1.413(3) . ?
C12 C13 1.427(3) . ?
C17 C16 1.356(3) . ?
C17 F2 1.357(3) . ?
C13 C14 1.353(3) . ?
C13 H13 0.9500 . ?
C14 F1 1.351(3) . ?
C14 C15 1.414(3) . ?
C21 N2 1.143(3) . ?
C21 C18 1.423(3) . ?
C23 N4 1.142(3) . ?
C23 C19 1.433(4) . ?
C20 N1 1.147(3) . ?
C20 C18 1.420(3) . ?
C19 C15 1.410(3) . ?
C19 C22 1.414(3) . ?
C22 N3 1.151(3) . ?
C2 C3 1.418(4) . ?
C2 C1 1.428(4) . ?
C2 Fe1 2.093(3) . ?
C2 H2 0.9500 . ?
C10 C9 1.422(3) . ?
C10 C6 1.424(3) . ?
C10 Fe1 2.078(2) . ?
C10 H10 0.9500 . ?
C7 C8 1.415(3) . ?
C7 C6 1.426(3) . ?
C7 Fe1 2.118(2) . ?
C7 H7 0.9500 . ?
C1 C5 1.422(4) . ?
C1 S1 1.726(3) . ?
C1 Fe1 2.144(3) . ?
C15 C16 1.417(3) . ?
C8 C9 1.421(4) . ?
C8 Fe1 2.082(3) . ?
C8 H8 0.9500 . ?
C3 C4 1.420(4) . ?
C3 Fe1 2.060(2) . ?
C3 H3 0.9500 . ?
C16 H16 0.9500 . ?
C5 C4 1.419(4) . ?
C5 Fe1 2.082(3) . ?
C5 H5 0.9500 . ?
C4 Fe1 2.057(3) . ?
C4 H4 0.9500 . ?
C6 C6 1.455(4) 2_675 ?
C6 Fe1 2.128(2) . ?
C9 Fe1 2.060(3) . ?
C9 H9 0.9500 . ?
C11 S1 1.800(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C17 C12 C18 123.8(2) . . ?
C17 C12 C13 114.9(2) . . ?
C18 C12 C13 121.3(2) . . ?
C16 C17 F2 117.9(2) . . ?
C16 C17 C12 124.9(2) . . ?
F2 C17 C12 117.1(2) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
F1 C14 C13 118.1(2) . . ?
F1 C14 C15 117.5(2) . . ?
C13 C14 C15 124.4(2) . . ?
N2 C21 C18 179.0(3) . . ?
N4 C23 C19 179.2(3) . . ?
N1 C20 C18 175.6(3) . . ?
C15 C19 C22 125.2(2) . . ?
C15 C19 C23 120.9(2) . . ?
C22 C19 C23 113.6(2) . . ?
N3 C22 C19 175.6(3) . . ?
C12 C18 C20 125.1(2) . . ?
C12 C18 C21 120.5(2) . . ?
C20 C18 C21 114.0(2) . . ?
C3 C2 C1 107.8(2) . . ?
C3 C2 Fe1 68.76(14) . . ?
C1 C2 Fe1 72.23(14) . . ?
C3 C2 H2 126.1 . . ?
C1 C2 H2 126.1 . . ?
Fe1 C2 H2 124.5 . . ?
C9 C10 C6 107.9(2) . . ?
C9 C10 Fe1 69.21(14) . . ?
C6 C10 Fe1 72.12(14) . . ?
C9 C10 H10 126.0 . . ?
C6 C10 H10 126.0 . . ?
Fe1 C10 H10 124.2 . . ?
C8 C7 C6 108.2(2) . . ?
C8 C7 Fe1 68.98(15) . . ?
C6 C7 Fe1 70.79(13) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
Fe1 C7 H7 125.9 . . ?
C5 C1 C2 107.7(2) . . ?
C5 C1 S1 123.1(2) . . ?
C2 C1 S1 129.2(2) . . ?
C5 C1 Fe1 68.02(14) . . ?
C2 C1 Fe1 68.41(14) . . ?
S1 C1 Fe1 126.23(13) . . ?
C19 C15 C14 124.2(2) . . ?
C19 C15 C16 120.5(2) . . ?
C14 C15 C16 115.2(2) . . ?
C7 C8 C9 108.1(2) . . ?
C7 C8 Fe1 71.66(15) . . ?
C9 C8 Fe1 69.09(15) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
Fe1 C8 H8 124.9 . . ?
C2 C3 C4 108.3(2) . . ?
C2 C3 Fe1 71.31(14) . . ?
C4 C3 Fe1 69.71(14) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Fe1 C3 H3 124.7 . . ?
C17 C16 C15 120.2(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C4 C5 C1 108.2(2) . . ?
C4 C5 Fe1 68.99(15) . . ?
C1 C5 Fe1 72.70(14) . . ?
C4 C5 H5 125.9 . . ?
C1 C5 H5 125.9 . . ?
Fe1 C5 H5 124.0 . . ?
C5 C4 C3 107.9(2) . . ?
C5 C4 Fe1 70.92(14) . . ?
C3 C4 Fe1 69.94(14) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
Fe1 C4 H4 124.7 . . ?
C10 C6 C7 107.7(2) . . ?
C10 C6 C6 126.3(3) . 2_675 ?
C7 C6 C6 125.8(3) . 2_675 ?
C10 C6 Fe1 68.32(13) . . ?
C7 C6 Fe1 69.97(13) . . ?
C6 C6 Fe1 123.8(2) 2_675 . ?
C8 C9 C10 108.0(2) . . ?
C8 C9 Fe1 70.78(15) . . ?
C10 C9 Fe1 70.58(14) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 124.3 . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 Fe1 C3 40.35(11) . . ?
C4 Fe1 C9 108.04(11) . . ?
C3 Fe1 C9 125.01(10) . . ?
C4 Fe1 C10 125.71(11) . . ?
C3 Fe1 C10 161.95(11) . . ?
C9 Fe1 C10 40.20(9) . . ?
C4 Fe1 C5 40.08(10) . . ?
C3 Fe1 C5 67.30(11) . . ?
C9 Fe1 C5 121.95(11) . . ?
C10 Fe1 C5 109.50(10) . . ?
C4 Fe1 C8 121.30(10) . . ?
C3 Fe1 C8 108.17(11) . . ?
C9 Fe1 C8 40.13(11) . . ?
C10 Fe1 C8 67.16(10) . . ?
C5 Fe1 C8 156.38(11) . . ?
C4 Fe1 C2 67.30(11) . . ?
C3 Fe1 C2 39.93(10) . . ?
C9 Fe1 C2 161.55(10) . . ?
C10 Fe1 C2 156.96(10) . . ?
C5 Fe1 C2 66.87(10) . . ?
C8 Fe1 C2 125.58(11) . . ?
C4 Fe1 C7 155.92(11) . . ?
C3 Fe1 C7 121.80(11) . . ?
C9 Fe1 C7 66.66(10) . . ?
C10 Fe1 C7 66.52(10) . . ?
C5 Fe1 C7 162.93(10) . . ?
C8 Fe1 C7 39.36(9) . . ?
C2 Fe1 C7 109.81(10) . . ?
C4 Fe1 C6 162.58(11) . . ?
C3 Fe1 C6 156.40(11) . . ?
C9 Fe1 C6 66.66(9) . . ?
C10 Fe1 C6 39.56(9) . . ?
C5 Fe1 C6 127.17(10) . . ?
C8 Fe1 C6 66.24(9) . . ?
C2 Fe1 C6 123.02(10) . . ?
C7 Fe1 C6 39.24(9) . . ?
C4 Fe1 C1 66.39(10) . . ?
C3 Fe1 C1 66.31(10) . . ?
C9 Fe1 C1 157.01(11) . . ?
C10 Fe1 C1 123.35(10) . . ?
C5 Fe1 C1 39.29(10) . . ?
C8 Fe1 C1 162.22(11) . . ?
C2 Fe1 C1 39.36(10) . . ?
C7 Fe1 C1 127.62(10) . . ?
C6 Fe1 C1 111.53(9) . . ?
C1 S1 C11 102.09(13) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        28.22
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.900
_refine_diff_density_min         -1.060
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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_4c
_database_code_depnum_ccdc_archive 'CCDC 1499550'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H26 Fe2, 2(C12 H2 F2 N4)'
_chemical_formula_sum            'C48 H30 F4 Fe2 N8'
_chemical_formula_weight         906.50

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'
F F 0.0171 0.0103 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7951(13)
_cell_length_b                   9.1673(13)
_cell_length_c                   13.4002(18)
_cell_angle_alpha                92.358(12)
_cell_angle_beta                 104.633(12)
_cell_angle_gamma                109.317(11)
_cell_volume                     977.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      14.8
_cell_measurement_theta_max      15.0
_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             462
_exptl_absorpt_coefficient_mu    0.810
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8548
_exptl_absorpt_correction_T_max  0.8548
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       ω-2θ
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            4780
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4487
_reflns_number_gt                3842
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_structure_solution    SIR92
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_molecular_graphics    ?
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0278P)²+0.6341P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4487
_refine_ls_number_parameters     284
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 1.0537(8) 0.6297(6) 0.1319(5) 0.0616(6) Uani 0.454(4) 1 d PU A 1
H12A H 1.0783 0.6016 0.2009 0.092 Uiso 0.454(4) 1 calc PR A 1
H12B H 1.1285 0.7331 0.1316 0.092 Uiso 0.454(4) 1 calc PR A 1
H12C H 1.0681 0.5573 0.0845 0.092 Uiso 0.454(4) 1 calc PR A 1
C13 C 0.7958(7) 0.5403(6) 0.0089(4) 0.0634(13) Uani 0.546(4) 1 d PU A 2
H13A H 0.6845 0.4876 0.0142 0.095 Uiso 0.546(4) 1 calc PR A 2
H13B H 0.8412 0.4649 -0.0100 0.095 Uiso 0.546(4) 1 calc PR A 2
H13C H 0.7917 0.6088 -0.0432 0.095 Uiso 0.546(4) 1 calc PR A 2
C11 C 0.8956(4) 0.6254(3) 0.1026(2) 0.0616(6) Uani 1 1 d U . .
H11A H 0.8240 0.5180 0.0997 0.074 Uiso 0.454(4) 1 calc PR A 1
H11B H 0.8743 0.6499 0.0319 0.074 Uiso 0.454(4) 1 calc PR A 1
H11C H 0.9986 0.6931 0.0906 0.074 Uiso 0.546(4) 1 d PR A 2
H11D H 0.9256 0.5530 0.1476 0.074 Uiso 0.546(4) 1 d PR A 2
C1 C 0.9695(2) 1.0449(2) 0.03157(14) 0.0299(4) Uani 1 1 d . . .
C2 C 1.0629(3) 1.1377(2) 0.12993(15) 0.0370(4) Uani 1 1 d . . .
H2 H 1.1804 1.1553 0.1661 0.044 Uiso 1 1 calc R . .
C3 C 0.9576(3) 1.2023(2) 0.16516(17) 0.0436(5) Uani 1 1 d . . .
H3 H 0.9897 1.2736 0.2296 0.052 Uiso 1 1 calc R . .
C4 C 0.7987(3) 1.1490(3) 0.09000(17) 0.0444(5) Uani 1 1 d . . .
H4 H 0.7018 1.1773 0.0934 0.053 Uiso 1 1 calc R . .
C5 C 0.8048(3) 1.0508(2) 0.00755(15) 0.0381(4) Uani 1 1 d . . .
H5 H 0.7131 0.9988 -0.0555 0.046 Uiso 1 1 calc R . .
C6 C 0.8350(3) 0.7255(2) 0.16304(17) 0.0418(5) Uani 1 1 d . A .
C7 C 0.9298(3) 0.8240(3) 0.25852(17) 0.0485(5) Uani 1 1 d . . .
H7 H 1.0464 0.8392 0.2956 0.058 Uiso 1 1 calc R A .
C8 C 0.8286(4) 0.8952(3) 0.29154(18) 0.0562(6) Uani 1 1 d . A .
H8 H 0.8610 0.9660 0.3562 0.067 Uiso 1 1 calc R . .
C9 C 0.6703(3) 0.8426(3) 0.2166(2) 0.0579(7) Uani 1 1 d . . .
H9 H 0.5731 0.8700 0.2203 0.070 Uiso 1 1 calc R A .
C10 C 0.6747(3) 0.7385(3) 0.13665(19) 0.0494(5) Uani 1 1 d . A .
H10 H 0.5815 0.6830 0.0750 0.059 Uiso 1 1 calc R . .
C14 C 0.4877(2) 0.2555(2) 0.49803(14) 0.0295(4) Uani 1 1 d . . .
C15 C 0.3251(2) 0.2643(2) 0.47238(14) 0.0341(4) Uani 1 1 d . . .
C16 C 0.2741(2) 0.3528(2) 0.53066(14) 0.0342(4) Uani 1 1 d . . .
H16 H 0.1646 0.3520 0.5090 0.041 Uiso 1 1 calc R . .
C17 C 0.3859(2) 0.4467(2) 0.62431(13) 0.0287(4) Uani 1 1 d . . .
C18 C 0.5475(2) 0.4358(2) 0.65082(15) 0.0354(4) Uani 1 1 d . . .
C19 C 0.5980(2) 0.3469(2) 0.59278(15) 0.0358(4) Uani 1 1 d . . .
H19 H 0.7066 0.3456 0.6154 0.043 Uiso 1 1 calc R . .
C20 C 0.5407(2) 0.1650(2) 0.43544(15) 0.0338(4) Uani 1 1 d . . .
C21 C 0.4383(3) 0.0671(2) 0.34125(16) 0.0401(4) Uani 1 1 d . . .
C22 C 0.7043(3) 0.1566(2) 0.46936(16) 0.0384(4) Uani 1 1 d . . .
C23 C 0.3353(2) 0.5418(2) 0.68537(14) 0.0312(4) Uani 1 1 d . . .
C24 C 0.1674(3) 0.5400(2) 0.65657(15) 0.0366(4) Uani 1 1 d . . .
C25 C 0.4347(3) 0.6318(2) 0.78289(16) 0.0382(4) Uani 1 1 d . . .
F1 F 0.21390(17) 0.17974(18) 0.38265(10) 0.0588(4) Uani 1 1 d . . .
F2 F 0.65929(16) 0.52266(19) 0.73967(11) 0.0660(4) Uani 1 1 d . . .
Fe1 Fe 0.85261(4) 0.95991(3) 0.14828(2) 0.03111(8) Uani 1 1 d . A .
N1 N 0.3638(3) -0.0147(3) 0.26459(16) 0.0577(5) Uani 1 1 d . . .
N2 N 0.8338(3) 0.1464(3) 0.49533(16) 0.0560(5) Uani 1 1 d . . .
N3 N 0.0329(2) 0.5397(3) 0.63721(16) 0.0542(5) Uani 1 1 d . . .
N4 N 0.5049(3) 0.7055(3) 0.86271(16) 0.0559(5) 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
C12 C11 1.332(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 H11C 0.9783 . ?
C12 H11D 1.1895 . ?
C13 C11 1.365(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 C6 1.504(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C1 C2 1.426(3) . ?
C1 C5 1.422(3) . ?
C1 C1 1.464(3) 2_775 ?
C1 Fe1 2.1194(17) . ?
C2 C3 1.411(3) . ?
C2 Fe1 2.099(2) . ?
C2 H2 0.9800 . ?
C3 C4 1.415(3) . ?
C3 Fe1 2.082(2) . ?
C3 H3 0.9800 . ?
C4 C5 1.419(3) . ?
C4 Fe1 2.075(2) . ?
C4 H4 0.9800 . ?
C5 Fe1 2.094(2) . ?
C5 H5 0.9800 . ?
C6 C10 1.410(3) . ?
C6 C7 1.419(3) . ?
C6 Fe1 2.124(2) . ?
C7 C8 1.405(3) . ?
C7 Fe1 2.098(2) . ?
C7 H7 0.9800 . ?
C8 C9 1.410(4) . ?
C8 Fe1 2.073(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.421(3) . ?
C9 Fe1 2.061(2) . ?
C9 H9 0.9800 . ?
C10 Fe1 2.084(2) . ?
C10 H10 0.9800 . ?
C14 C15 1.415(3) . ?
C14 C20 1.416(2) . ?
C14 C19 1.417(3) . ?
C15 C16 1.354(3) . ?
C15 F1 1.353(2) . ?
C16 C17 1.418(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.413(3) . ?
C17 C23 1.418(2) . ?
C18 C19 1.352(3) . ?
C18 F2 1.353(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.417(3) . ?
C20 C22 1.424(3) . ?
C21 N1 1.148(3) . ?
C22 N2 1.141(3) . ?
C23 C25 1.418(3) . ?
C23 C24 1.423(3) . ?
C24 N3 1.144(3) . ?
C25 N4 1.146(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
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H11C 46.6 . . ?
H12A C12 H11C 141.4 . . ?
H12B C12 H11C 66.5 . . ?
H12C C12 H11C 107.7 . . ?
C11 C12 H11D 44.8 . . ?
H12A C12 H11D 71.4 . . ?
H12B C12 H11D 146.0 . . ?
H12C C12 H11D 101.5 . . ?
H11C C12 H11D 91.4 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C11 C13 117.2(4) . . ?
C12 C11 C6 121.6(3) . . ?
C13 C11 C6 120.8(3) . . ?
C12 C11 H11A 106.9 . . ?
C13 C11 H11A 60.1 . . ?
C6 C11 H11A 106.9 . . ?
C12 C11 H11B 106.9 . . ?
C13 C11 H11B 46.7 . . ?
C6 C11 H11B 106.9 . . ?
H11A C11 H11B 106.7 . . ?
C12 C11 H11C 47.1 . . ?
C13 C11 H11C 106.9 . . ?
C6 C11 H11C 107.1 . . ?
H11A C11 H11C 145.2 . . ?
H11B C11 H11C 69.6 . . ?
C12 C11 H11D 59.8 . . ?
C13 C11 H11D 107.3 . . ?
C6 C11 H11D 107.2 . . ?
H11A C11 H11D 55.5 . . ?
H11B C11 H11D 145.0 . . ?
H11C C11 H11D 106.8 . . ?
C2 C1 C5 107.70(16) . . ?
C2 C1 C1 126.1(2) . 2_775 ?
C5 C1 C1 126.1(2) . 2_775 ?
C2 C1 Fe1 69.47(10) . . ?
C5 C1 Fe1 69.34(11) . . ?
C1 C1 Fe1 125.03(17) 2_775 . ?
C3 C2 C1 108.16(18) . . ?
C3 C2 Fe1 69.64(12) . . ?
C1 C2 Fe1 71.01(11) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 125.9 . . ?
C4 C3 C2 108.05(18) . . ?
C4 C3 Fe1 69.85(12) . . ?
C2 C3 Fe1 70.92(11) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.0 . . ?
C3 C4 C5 108.39(18) . . ?
C3 C4 Fe1 70.36(12) . . ?
C5 C4 Fe1 70.82(11) . . ?
C3 C4 H4 125.8 . . ?
C5 C4 H4 125.8 . . ?
Fe1 C4 H4 125.8 . . ?
C4 C5 C1 107.69(18) . . ?
C4 C5 Fe1 69.38(12) . . ?
C1 C5 Fe1 71.23(11) . . ?
C4 C5 H5 126.1 . . ?
C1 C5 H5 126.1 . . ?
Fe1 C5 H5 126.1 . . ?
C10 C6 C7 107.3(2) . . ?
C10 C6 C11 126.9(2) . . ?
C7 C6 C11 125.8(2) . . ?
C10 C6 Fe1 68.90(12) . . ?
C7 C6 Fe1 69.36(12) . . ?
C11 C6 Fe1 127.37(15) . . ?
C8 C7 C6 108.8(2) . . ?
C8 C7 Fe1 69.38(13) . . ?
C6 C7 Fe1 71.35(12) . . ?
C8 C7 H7 125.6 . . ?
C6 C7 H7 125.6 . . ?
Fe1 C7 H7 125.6 . . ?
C9 C8 C7 107.7(2) . . ?
C9 C8 Fe1 69.59(13) . . ?
C7 C8 Fe1 71.26(12) . . ?
C9 C8 H8 126.1 . . ?
C7 C8 H8 126.1 . . ?
Fe1 C8 H8 126.1 . . ?
C8 C9 C10 108.1(2) . . ?
C8 C9 Fe1 70.53(13) . . ?
C10 C9 Fe1 70.82(13) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
Fe1 C9 H9 125.9 . . ?
C6 C10 C9 108.1(2) . . ?
C6 C10 Fe1 71.95(12) . . ?
C9 C10 Fe1 69.08(13) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
C15 C14 C20 124.06(17) . . ?
C15 C14 C19 114.62(16) . . ?
C20 C14 C19 121.32(17) . . ?
C16 C15 F1 118.03(17) . . ?
C16 C15 C14 124.55(17) . . ?
F1 C15 C14 117.42(16) . . ?
C15 C16 C17 120.66(17) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C23 123.86(17) . . ?
C18 C17 C16 114.78(16) . . ?
C23 C17 C16 121.36(17) . . ?
C19 C18 F2 118.21(17) . . ?
C19 C18 C17 124.49(18) . . ?
F2 C18 C17 117.30(16) . . ?
C18 C19 C14 120.88(18) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C14 C20 C21 125.31(18) . . ?
C14 C20 C22 120.51(17) . . ?
C21 C20 C22 113.99(17) . . ?
N1 C21 C20 175.7(2) . . ?
N2 C22 C20 178.4(2) . . ?
C17 C23 C25 125.28(17) . . ?
C17 C23 C24 120.59(17) . . ?
C25 C23 C24 113.79(16) . . ?
N3 C24 C23 177.5(2) . . ?
N4 C25 C23 175.2(2) . . ?
C9 Fe1 C8 39.88(11) . . ?
C9 Fe1 C4 108.76(10) . . ?
C8 Fe1 C4 123.38(9) . . ?
C9 Fe1 C3 123.23(9) . . ?
C8 Fe1 C3 108.20(9) . . ?
C4 Fe1 C3 39.80(9) . . ?
C9 Fe1 C10 40.11(10) . . ?
C8 Fe1 C10 66.91(10) . . ?
C4 Fe1 C10 124.63(10) . . ?
C3 Fe1 C10 159.37(9) . . ?
C9 Fe1 C7 66.27(11) . . ?
C8 Fe1 C7 39.36(10) . . ?
C4 Fe1 C7 158.64(9) . . ?
C3 Fe1 C7 123.85(9) . . ?
C10 Fe1 C7 66.05(10) . . ?
C9 Fe1 C5 124.40(10) . . ?
C8 Fe1 C5 159.18(9) . . ?
C4 Fe1 C5 39.80(8) . . ?
C3 Fe1 C5 66.79(9) . . ?
C10 Fe1 C5 110.17(9) . . ?
C7 Fe1 C5 160.30(8) . . ?
C9 Fe1 C2 158.34(9) . . ?
C8 Fe1 C2 123.44(10) . . ?
C4 Fe1 C2 66.44(9) . . ?
C3 Fe1 C2 39.44(8) . . ?
C10 Fe1 C2 160.12(8) . . ?
C7 Fe1 C2 109.96(9) . . ?
C5 Fe1 C2 66.52(8) . . ?
C9 Fe1 C6 66.40(9) . . ?
C8 Fe1 C6 66.34(9) . . ?
C4 Fe1 C6 160.07(9) . . ?
C3 Fe1 C6 159.33(9) . . ?
C10 Fe1 C6 39.15(9) . . ?
C7 Fe1 C6 39.29(9) . . ?
C5 Fe1 C6 125.45(8) . . ?
C2 Fe1 C6 125.32(8) . . ?
C9 Fe1 C1 160.16(10) . . ?
C8 Fe1 C1 159.18(10) . . ?
C4 Fe1 C1 66.30(8) . . ?
C3 Fe1 C1 66.30(7) . . ?
C10 Fe1 C1 125.36(8) . . ?
C7 Fe1 C1 125.43(9) . . ?
C5 Fe1 C1 39.43(7) . . ?
C2 Fe1 C1 39.52(7) . . ?
C6 Fe1 C1 111.21(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1499546'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Fe2 S2, 2(C12 H3 Cl N4)'
_chemical_formula_sum            'C46 H28 Cl2 Fe2 N8 S2'
_chemical_formula_weight         939.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8205(8)
_cell_length_b                   9.0902(8)
_cell_length_c                   13.6352(13)
_cell_angle_alpha                90.168(2)
_cell_angle_beta                 104.444(2)
_cell_angle_gamma                107.949(2)
_cell_volume                     1003.40(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7521
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            7478
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4941
_reflns_number_gt                3988
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0890P)²+1.6292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4941
_refine_ls_number_parameters     282
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_ref         0.1809
_refine_ls_wR_factor_gt          0.1705
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.6617(4) 0.1645(4) 0.37266(19) 0.0798(11) Uani 0.499(4) 1 d P A 1
Cl2 Cl 1.1787(3) 0.5523(3) 0.74111(18) 0.0595(8) Uani 0.501(4) 1 d P A 2
C1 C 0.7020(6) 0.2824(4) 0.8543(3) 0.0471(10) Uani 1 1 d . . .
C2 C 0.6100(6) 0.1870(5) 0.7627(3) 0.0488(10) Uani 1 1 d . . .
H2 H 0.4947 0.1777 0.7238 0.059 Uiso 1 1 calc R . .
C3 C 0.7139(7) 0.1114(5) 0.7347(3) 0.0547(12) Uani 1 1 d . . .
H3 H 0.6840 0.0396 0.6722 0.066 Uiso 1 1 calc R . .
C4 C 0.8668(7) 0.1561(5) 0.8088(4) 0.0572(12) Uani 1 1 d . . .
H4 H 0.9639 0.1217 0.8082 0.069 Uiso 1 1 calc R . .
C5 C 0.8588(6) 0.2608(5) 0.8847(4) 0.0535(11) Uani 1 1 d . . .
H5 H 0.9488 0.3116 0.9469 0.064 Uiso 1 1 calc R . .
C6 C 0.5405(5) -0.0428(4) 0.9769(3) 0.0362(8) Uani 1 1 d . . .
C7 C 0.4726(6) -0.1336(4) 0.8815(3) 0.0424(9) Uani 1 1 d . . .
H7 H 0.3578 -0.1552 0.8372 0.051 Uiso 1 1 calc R . .
C8 C 0.5957(6) -0.1909(4) 0.8616(3) 0.0497(10) Uani 1 1 d . . .
H8 H 0.5819 -0.2599 0.8006 0.060 Uiso 1 1 calc R . .
C9 C 0.7407(6) -0.1344(5) 0.9417(3) 0.0493(10) Uani 1 1 d . . .
H9 H 0.8466 -0.1569 0.9477 0.059 Uiso 1 1 calc R . .
C10 C 0.7093(5) -0.0397(4) 1.0125(3) 0.0425(8) Uani 1 1 d . . .
H10 H 0.7896 0.0163 1.0771 0.051 Uiso 1 1 calc R . .
C11 C 0.4408(8) 0.3728(6) 0.8637(4) 0.0706(15) Uani 1 1 d . . .
H11A H 0.4303 0.4012 0.7937 0.106 Uiso 1 1 calc R . .
H11B H 0.3948 0.4347 0.8996 0.106 Uiso 1 1 calc R . .
H11C H 0.3805 0.2623 0.8633 0.106 Uiso 1 1 calc R . .
C12 C 0.8719(5) 0.4374(4) 0.6234(3) 0.0371(7) Uani 1 1 d . . .
C13 C 0.7561(5) 0.3387(5) 0.5374(3) 0.0417(8) Uani 1 1 d . A .
H13 H 0.6437 0.3349 0.5214 0.050 Uiso 1 1 calc R . .
C14 C 0.8040(5) 0.2514(5) 0.4789(3) 0.0427(8) Uani 1 1 d . . .
H14 H 0.7240 0.1881 0.4222 0.051 Uiso 0.501(4) 1 calc PR A 2
C15 C 0.9708(5) 0.2505(4) 0.4992(3) 0.0393(8) Uani 1 1 d . A .
C16 C 1.0855(5) 0.3471(4) 0.5855(3) 0.0434(8) Uani 1 1 d . . .
H16 H 1.1977 0.3502 0.6020 0.052 Uiso 1 1 calc R A .
C17 C 1.0372(5) 0.4344(4) 0.6442(3) 0.0417(8) Uani 1 1 d . A .
H17 H 1.1168 0.4963 0.7017 0.050 Uiso 0.499(4) 1 calc PR A 1
C18 C 0.8178(5) 0.5284(4) 0.6808(3) 0.0440(9) Uani 1 1 d . . .
C19 C 1.0248(6) 0.1600(4) 0.4403(3) 0.0442(9) Uani 1 1 d . . .
C20 C 0.9184(7) 0.6276(5) 0.7682(4) 0.0659(14) Uani 1 1 d U . .
C21 C 0.6495(6) 0.5254(5) 0.6562(3) 0.0519(10) Uani 1 1 d . . .
C22 C 0.9233(7) 0.0594(5) 0.3537(3) 0.0540(11) Uani 1 1 d . A .
C23 C 1.1912(7) 0.1588(5) 0.4664(4) 0.0537(11) Uani 1 1 d . A .
Fe1 Fe 0.67766(7) 0.04697(5) 0.87281(4) 0.03606(18) Uani 1 1 d . . .
N1 N 0.9968(9) 0.7072(7) 0.8406(5) 0.120(2) Uani 1 1 d U . .
N2 N 0.5146(6) 0.5226(6) 0.6380(3) 0.0694(12) Uani 1 1 d . . .
N3 N 0.8459(8) -0.0244(6) 0.2842(3) 0.0829(15) Uani 1 1 d . . .
N4 N 1.3233(6) 0.1542(5) 0.4865(4) 0.0736(13) Uani 1 1 d . . .
S2 S 0.6481(2) 0.40833(13) 0.92520(11) 0.0656(4) 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
Cl1 C14 1.665(5) . ?
Cl2 C17 1.672(4) . ?
C1 C5 1.416(7) . ?
C1 C2 1.423(6) . ?
C1 S2 1.741(4) . ?
C1 Fe1 2.106(4) . ?
C2 C3 1.421(6) . ?
C2 Fe1 2.065(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.409(8) . ?
C3 Fe1 2.046(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.433(6) . ?
C4 Fe1 2.060(4) . ?
C4 H4 1.0000 . ?
C5 Fe1 2.077(4) . ?
C5 H5 1.0000 . ?
C6 C7 1.426(5) . ?
C6 C10 1.437(6) . ?
C6 C6 1.441(7) 2_657 ?
C6 Fe1 2.097(3) . ?
C7 C8 1.421(6) . ?
C7 Fe1 2.064(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.409(7) . ?
C8 Fe1 2.049(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.424(5) . ?
C9 Fe1 2.055(4) . ?
C9 H9 1.0000 . ?
C10 Fe1 2.051(4) . ?
C10 H10 1.0000 . ?
C11 S2 1.737(7) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.397(5) . ?
C12 C17 1.423(6) . ?
C12 C13 1.434(5) . ?
C13 C14 1.348(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.430(6) . ?
C14 H14 0.9500 . ?
C15 C19 1.406(5) . ?
C15 C16 1.425(6) . ?
C16 C17 1.353(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C20 1.412(6) . ?
C18 C21 1.429(6) . ?
C19 C22 1.412(6) . ?
C19 C23 1.425(7) . ?
C20 N1 1.151(7) . ?
C21 N2 1.146(6) . ?
C22 N3 1.139(6) . ?
C23 N4 1.143(6) . ?

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
C5 C1 C2 108.3(4) . . ?
C5 C1 S2 121.4(4) . . ?
C2 C1 S2 130.3(4) . . ?
C5 C1 Fe1 69.1(2) . . ?
C2 C1 Fe1 68.5(2) . . ?
S2 C1 Fe1 127.9(2) . . ?
C3 C2 C1 107.5(4) . . ?
C3 C2 Fe1 69.1(2) . . ?
C1 C2 Fe1 71.6(2) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.7(4) . . ?
C4 C3 Fe1 70.5(2) . . ?
C2 C3 Fe1 70.5(2) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 125.6 . . ?
C3 C4 C5 107.8(4) . . ?
C3 C4 Fe1 69.4(2) . . ?
C5 C4 Fe1 70.4(2) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
Fe1 C4 H4 126.1 . . ?
C1 C5 C4 107.7(4) . . ?
C1 C5 Fe1 71.3(2) . . ?
C4 C5 Fe1 69.1(2) . . ?
C1 C5 H5 126.2 . . ?
C4 C5 H5 126.2 . . ?
Fe1 C5 H5 126.2 . . ?
C7 C6 C10 107.2(3) . . ?
C7 C6 C6 125.9(5) . 2_657 ?
C10 C6 C6 126.6(4) . 2_657 ?
C7 C6 Fe1 68.7(2) . . ?
C10 C6 Fe1 68.00(19) . . ?
C6 C6 Fe1 123.7(3) 2_657 . ?
C8 C7 C6 107.9(4) . . ?
C8 C7 Fe1 69.3(2) . . ?
C6 C7 Fe1 71.2(2) . . ?
C8 C7 H7 126.1 . . ?
C6 C7 H7 126.1 . . ?
Fe1 C7 H7 126.1 . . ?
C9 C8 C7 109.0(3) . . ?
C9 C8 Fe1 70.1(2) . . ?
C7 C8 Fe1 70.3(2) . . ?
C9 C8 H8 125.5 . . ?
C7 C8 H8 125.5 . . ?
Fe1 C8 H8 125.5 . . ?
C8 C9 C10 107.7(4) . . ?
C8 C9 Fe1 69.7(2) . . ?
C10 C9 Fe1 69.6(2) . . ?
C8 C9 H9 126.2 . . ?
C10 C9 H9 126.2 . . ?
Fe1 C9 H9 126.2 . . ?
C9 C10 C6 108.2(4) . . ?
C9 C10 Fe1 69.9(2) . . ?
C6 C10 Fe1 71.5(2) . . ?
C9 C10 H10 125.9 . . ?
C6 C10 H10 125.9 . . ?
Fe1 C10 H10 125.9 . . ?
S2 C11 H11A 109.5 . . ?
S2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C12 C17 124.5(4) . . ?
C18 C12 C13 119.2(4) . . ?
C17 C12 C13 116.3(3) . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 122.4(4) . . ?
C13 C14 Cl1 114.9(3) . . ?
C15 C14 Cl1 122.1(3) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
Cl1 C14 H14 8.3 . . ?
C19 C15 C16 119.6(4) . . ?
C19 C15 C14 123.9(4) . . ?
C16 C15 C14 116.5(3) . . ?
C17 C16 C15 121.0(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C12 122.6(4) . . ?
C16 C17 Cl2 119.0(3) . . ?
C12 C17 Cl2 118.2(3) . . ?
C16 C17 H17 118.7 . . ?
C12 C17 H17 118.7 . . ?
Cl2 C17 H17 3.4 . . ?
C12 C18 C20 124.8(4) . . ?
C12 C18 C21 121.7(4) . . ?
C20 C18 C21 113.5(4) . . ?
C15 C19 C22 124.9(4) . . ?
C15 C19 C23 121.6(4) . . ?
C22 C19 C23 113.4(4) . . ?
N1 C20 C18 178.1(6) . . ?
N2 C21 C18 179.0(5) . . ?
N3 C22 C19 177.4(5) . . ?
N4 C23 C19 178.4(5) . . ?
C3 Fe1 C8 106.71(17) . . ?
C3 Fe1 C10 160.78(18) . . ?
C8 Fe1 C10 67.82(17) . . ?
C3 Fe1 C9 123.48(17) . . ?
C8 Fe1 C9 40.16(19) . . ?
C10 Fe1 C9 40.58(15) . . ?
C3 Fe1 C4 40.1(2) . . ?
C8 Fe1 C4 118.03(17) . . ?
C10 Fe1 C4 124.6(2) . . ?
C9 Fe1 C4 105.44(19) . . ?
C3 Fe1 C7 120.51(19) . . ?
C8 Fe1 C7 40.42(16) . . ?
C10 Fe1 C7 68.12(17) . . ?
C9 Fe1 C7 68.02(18) . . ?
C4 Fe1 C7 153.40(18) . . ?
C3 Fe1 C2 40.44(17) . . ?
C8 Fe1 C2 126.34(19) . . ?
C10 Fe1 C2 157.29(16) . . ?
C9 Fe1 C2 161.52(17) . . ?
C4 Fe1 C2 67.8(2) . . ?
C7 Fe1 C2 109.86(19) . . ?
C3 Fe1 C5 67.68(19) . . ?
C8 Fe1 C5 153.01(19) . . ?
C10 Fe1 C5 108.31(19) . . ?
C9 Fe1 C5 119.3(2) . . ?
C4 Fe1 C5 40.54(18) . . ?
C7 Fe1 C5 165.25(16) . . ?
C2 Fe1 C5 67.5(2) . . ?
C3 Fe1 C6 156.27(19) . . ?
C8 Fe1 C6 67.40(14) . . ?
C10 Fe1 C6 40.53(16) . . ?
C9 Fe1 C6 67.84(15) . . ?
C4 Fe1 C6 163.3(2) . . ?
C7 Fe1 C6 40.07(14) . . ?
C2 Fe1 C6 123.24(16) . . ?
C5 Fe1 C6 128.10(16) . . ?
C3 Fe1 C1 67.02(16) . . ?
C8 Fe1 C1 164.6(2) . . ?
C10 Fe1 C1 122.75(16) . . ?
C9 Fe1 C1 155.1(2) . . ?
C4 Fe1 C1 67.02(17) . . ?
C7 Fe1 C1 129.27(17) . . ?
C2 Fe1 C1 39.87(17) . . ?
C5 Fe1 C1 39.57(18) . . ?
C6 Fe1 C1 112.27(14) . . ?
C11 S2 C1 102.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         1.550
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.103
####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 1499548'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Fe2 S2, 2(C12 H2 Cl2 N4)'
_chemical_formula_sum            'C46 H26 Cl4 Fe2 N8 S2'
_chemical_formula_weight         1008.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'




loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8175(12)
_cell_length_b                   9.1617(12)
_cell_length_c                   13.8108(18)
_cell_angle_alpha                90.540(2)
_cell_angle_beta                 103.988(2)
_cell_angle_gamma                109.5500(10)
_cell_volume                     1015.2(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150
_cell_measurement_reflns_used    1638

_cell_measurement_theta_min      2.60

_cell_measurement_theta_max      27.87



_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             510
_exptl_absorpt_coefficient_mu    1.129
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8955
_exptl_absorpt_correction_T_max  0.9457
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            4872
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3535
_reflns_number_gt                2914
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.6545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3535
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.19551(5) 0.05654(5) 0.38215(3) 0.01703(13) Uani 1 1 d . . .
Cl1 Cl 0.11967(9) 0.12188(9) -0.11978(6) 0.0273(2) Uani 1 1 d . . .
Cl2 Cl 0.67495(9) 0.54432(10) 0.23972(6) 0.0298(2) Uani 1 1 d . . .
S1 S 0.17181(11) 0.41507(10) 0.44080(7) 0.0325(2) Uani 1 1 d . . .
C16 C 0.5634(3) 0.3440(3) 0.0772(2) 0.0191(6) Uani 1 1 d . . .
H16 H 0.6759 0.3486 0.0915 0.023 Uiso 1 1 calc R . .
C6 C 0.0411(4) -0.0414(3) 0.4767(2) 0.0184(6) Uani 1 1 d . . .
C14 C 0.2768(3) 0.2412(3) -0.0225(2) 0.0169(6) Uani 1 1 d . . .
C12 C 0.3559(3) 0.4376(3) 0.1191(2) 0.0167(6) Uani 1 1 d . . .
C17 C 0.5217(3) 0.4340(3) 0.1375(2) 0.0175(6) Uani 1 1 d . . .
C13 C 0.2359(4) 0.3327(3) 0.0362(2) 0.0174(6) Uani 1 1 d . . .
H13 H 0.1232 0.3276 0.0222 0.021 Uiso 1 1 calc R . .
C1 C 0.2335(4) 0.2952(3) 0.3717(2) 0.0229(7) Uani 1 1 d . . .
C15 C 0.4448(3) 0.2427(3) -0.0068(2) 0.0169(6) Uani 1 1 d . . .
C18 C 0.3038(4) 0.5317(3) 0.1744(2) 0.0196(7) Uani 1 1 d . . .
C7 C -0.0222(4) -0.1260(3) 0.3798(2) 0.0208(7) Uani 1 1 d . . .
H7 H -0.1283 -0.1414 0.3355 0.025 Uiso 1 1 calc R . .
C9 C 0.2414(4) -0.1322(4) 0.4450(2) 0.0251(7) Uani 1 1 d . . .
H9 H 0.3410 -0.1547 0.4527 0.030 Uiso 1 1 calc R . .
C2 C 0.1478(4) 0.2053(3) 0.2773(2) 0.0240(7) Uani 1 1 d . . .
H2 H 0.0397 0.1965 0.2384 0.029 Uiso 1 1 calc R . .
C19 C 0.4985(4) 0.1533(3) -0.0647(2) 0.0204(7) Uani 1 1 d . . .
C5 C 0.3884(4) 0.2705(3) 0.4059(2) 0.0238(7) Uani 1 1 d . . .
H5 H 0.4689 0.3129 0.4679 0.029 Uiso 1 1 calc R . .
C22 C 0.3998(4) 0.0413(4) -0.1491(2) 0.0259(7) Uani 1 1 d . . .
C11 C -0.0401(4) 0.3779(4) 0.3707(3) 0.0347(8) Uani 1 1 d . . .
H11A H -0.0416 0.4118 0.3035 0.052 Uiso 1 1 calc R . .
H11B H -0.0907 0.4354 0.4052 0.052 Uiso 1 1 calc R . .
H11C H -0.1035 0.2662 0.3651 0.052 Uiso 1 1 calc R . .
C10 C 0.2076(4) -0.0418(3) 0.5156(2) 0.0216(7) Uani 1 1 d . . .
H10 H 0.2821 0.0096 0.5777 0.026 Uiso 1 1 calc R . .
C21 C 0.1322(4) 0.5188(3) 0.1489(2) 0.0224(7) Uani 1 1 d . . .
C20 C 0.4019(4) 0.6427(4) 0.2588(2) 0.0234(7) Uani 1 1 d . . .
C4 C 0.4008(4) 0.1715(4) 0.3309(3) 0.0274(7) Uani 1 1 d . . .
H4 H 0.4925 0.1379 0.3335 0.033 Uiso 1 1 calc R . .
C3 C 0.2539(4) 0.1310(4) 0.2516(2) 0.0257(7) Uani 1 1 d . . .
H3 H 0.2299 0.0660 0.1918 0.031 Uiso 1 1 calc R . .
C8 C 0.0996(4) -0.1833(3) 0.3605(2) 0.0251(7) Uani 1 1 d . . .
H8 H 0.0886 -0.2448 0.3018 0.030 Uiso 1 1 calc R . .
C23 C 0.6700(4) 0.1656(3) -0.0409(2) 0.0231(7) Uani 1 1 d . . .
N1 N 0.4660(4) 0.7353(4) 0.3264(2) 0.0387(7) Uani 1 1 d . . .
N2 N -0.0052(3) 0.5098(3) 0.1309(2) 0.0311(7) Uani 1 1 d . . .
N3 N 0.3364(4) -0.0509(4) -0.2163(2) 0.0392(8) Uani 1 1 d . . .
N4 N 0.8063(4) 0.1724(3) -0.0217(2) 0.0354(7) 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
Fe1 C3 2.054(3) . ?
Fe1 C10 2.054(3) . ?
Fe1 C9 2.058(3) . ?
Fe1 C4 2.060(3) . ?
Fe1 C8 2.063(3) . ?
Fe1 C2 2.064(3) . ?
Fe1 C7 2.074(3) . ?
Fe1 C5 2.081(3) . ?
Fe1 C6 2.105(3) . ?
Fe1 C1 2.110(3) . ?
Cl1 C14 1.726(3) . ?
Cl2 C17 1.726(3) . ?
S1 C1 1.745(3) . ?
S1 C11 1.800(3) . ?
C16 C17 1.358(4) . ?
C16 C15 1.430(4) . ?
C16 H16 0.9500 . ?
C6 C7 1.426(4) . ?
C6 C10 1.437(4) . ?
C6 C6 1.448(6) 2_556 ?
C14 C13 1.350(4) . ?
C14 C15 1.440(4) . ?
C12 C18 1.400(4) . ?
C12 C17 1.435(4) . ?
C12 C13 1.438(4) . ?
C13 H13 0.9500 . ?
C1 C2 1.427(4) . ?
C1 C5 1.427(4) . ?
C15 C19 1.401(4) . ?
C18 C20 1.429(4) . ?
C18 C21 1.431(4) . ?
C7 C8 1.418(4) . ?
C7 H7 0.9500 . ?
C9 C10 1.420(4) . ?
C9 C8 1.427(5) . ?
C9 H9 0.9500 . ?
C2 C3 1.431(4) . ?
C2 H2 0.9500 . ?
C19 C23 1.433(4) . ?
C19 C22 1.435(4) . ?
C5 C4 1.418(5) . ?
C5 H5 0.9500 . ?
C22 N3 1.143(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 H10 0.9500 . ?
C21 N2 1.150(4) . ?
C20 N1 1.149(4) . ?
C4 C3 1.415(5) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C8 H8 0.9500 . ?
C23 N4 1.147(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Fe1 C10 159.90(12) . . ?
C3 Fe1 C9 122.94(13) . . ?
C10 Fe1 C9 40.40(12) . . ?
C3 Fe1 C4 40.22(13) . . ?
C10 Fe1 C4 123.97(13) . . ?
C9 Fe1 C4 105.45(13) . . ?
C3 Fe1 C8 106.32(13) . . ?
C10 Fe1 C8 68.08(12) . . ?
C9 Fe1 C8 40.53(13) . . ?
C4 Fe1 C8 118.54(13) . . ?
C3 Fe1 C2 40.66(12) . . ?
C10 Fe1 C2 157.92(13) . . ?
C9 Fe1 C2 161.09(13) . . ?
C4 Fe1 C2 67.80(13) . . ?
C8 Fe1 C2 125.68(13) . . ?
C3 Fe1 C7 121.16(12) . . ?
C10 Fe1 C7 67.83(12) . . ?
C9 Fe1 C7 67.66(13) . . ?
C4 Fe1 C7 154.23(13) . . ?
C8 Fe1 C7 40.10(12) . . ?
C2 Fe1 C7 110.26(12) . . ?
C3 Fe1 C5 67.62(13) . . ?
C10 Fe1 C5 108.20(13) . . ?
C9 Fe1 C5 119.34(13) . . ?
C4 Fe1 C5 40.04(13) . . ?
C8 Fe1 C5 153.36(12) . . ?
C2 Fe1 C5 67.65(12) . . ?
C7 Fe1 C5 165.12(12) . . ?
C3 Fe1 C6 157.10(12) . . ?
C10 Fe1 C6 40.42(11) . . ?
C9 Fe1 C6 67.54(12) . . ?
C4 Fe1 C6 162.46(12) . . ?
C8 Fe1 C6 67.36(12) . . ?
C2 Fe1 C6 123.85(12) . . ?
C7 Fe1 C6 39.90(11) . . ?
C5 Fe1 C6 127.96(12) . . ?
C3 Fe1 C1 67.28(12) . . ?
C10 Fe1 C1 123.02(12) . . ?
C9 Fe1 C1 155.44(13) . . ?
C4 Fe1 C1 66.89(13) . . ?
C8 Fe1 C1 163.88(12) . . ?
C2 Fe1 C1 39.96(12) . . ?
C7 Fe1 C1 129.25(12) . . ?
C5 Fe1 C1 39.81(12) . . ?
C6 Fe1 C1 112.40(12) . . ?
C1 S1 C11 102.12(16) . . ?
C17 C16 C15 122.7(3) . . ?
C17 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C7 C6 C10 107.1(3) . . ?
C7 C6 C6 126.4(3) . 2_556 ?
C10 C6 C6 126.3(3) . 2_556 ?
C7 C6 Fe1 68.90(17) . . ?
C10 C6 Fe1 67.90(16) . . ?
C6 C6 Fe1 124.1(3) 2_556 . ?
C13 C14 C15 122.2(3) . . ?
C13 C14 Cl1 117.5(2) . . ?
C15 C14 Cl1 120.3(2) . . ?
C18 C12 C17 125.9(3) . . ?
C18 C12 C13 119.0(3) . . ?
C17 C12 C13 115.1(3) . . ?
C16 C17 C12 122.1(3) . . ?
C16 C17 Cl2 118.0(2) . . ?
C12 C17 Cl2 119.9(2) . . ?
C14 C13 C12 122.7(3) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C2 C1 C5 107.9(3) . . ?
C2 C1 S1 129.6(2) . . ?
C5 C1 S1 122.5(2) . . ?
C2 C1 Fe1 68.27(16) . . ?
C5 C1 Fe1 68.99(16) . . ?
S1 C1 Fe1 127.47(16) . . ?
C19 C15 C16 118.9(3) . . ?
C19 C15 C14 125.9(3) . . ?
C16 C15 C14 115.1(3) . . ?
C12 C18 C20 127.9(3) . . ?
C12 C18 C21 119.5(3) . . ?
C20 C18 C21 112.6(3) . . ?
C8 C7 C6 108.7(3) . . ?
C8 C7 Fe1 69.51(17) . . ?
C6 C7 Fe1 71.20(17) . . ?
C8 C7 H7 125.7 . . ?
C6 C7 H7 125.7 . . ?
Fe1 C7 H7 125.2 . . ?
C10 C9 C8 108.1(3) . . ?
C10 C9 Fe1 69.67(17) . . ?
C8 C9 Fe1 69.93(17) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
Fe1 C9 H9 126.0 . . ?
C1 C2 C3 107.7(3) . . ?
C1 C2 Fe1 71.77(17) . . ?
C3 C2 Fe1 69.29(17) . . ?
C1 C2 H2 126.2 . . ?
C3 C2 H2 126.2 . . ?
Fe1 C2 H2 124.4 . . ?
C15 C19 C23 120.4(3) . . ?
C15 C19 C22 127.8(3) . . ?
C23 C19 C22 111.8(3) . . ?
C4 C5 C1 107.8(3) . . ?
C4 C5 Fe1 69.18(17) . . ?
C1 C5 Fe1 71.20(17) . . ?
C4 C5 H5 126.1 . . ?
C1 C5 H5 126.1 . . ?
Fe1 C5 H5 125.1 . . ?
N3 C22 C19 172.7(4) . . ?
S1 C11 H11A 109.5 . . ?
S1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
S1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 C6 108.2(3) . . ?
C9 C10 Fe1 69.93(17) . . ?
C6 C10 Fe1 71.68(16) . . ?
C9 C10 H10 125.9 . . ?
C6 C10 H10 125.9 . . ?
Fe1 C10 H10 124.1 . . ?
N2 C21 C18 178.3(3) . . ?
N1 C20 C18 172.9(3) . . ?
C3 C4 C5 108.7(3) . . ?
C3 C4 Fe1 69.66(17) . . ?
C5 C4 Fe1 70.78(17) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Fe1 C4 H4 125.5 . . ?
C4 C3 C2 107.9(3) . . ?
C4 C3 Fe1 70.11(18) . . ?
C2 C3 Fe1 70.05(17) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
Fe1 C3 H3 125.4 . . ?
C7 C8 C9 107.9(3) . . ?
C7 C8 Fe1 70.39(17) . . ?
C9 C8 Fe1 69.54(17) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
Fe1 C8 H8 125.6 . . ?
N4 C23 C19 178.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.075
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1499544'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Fe2 Se2, 2(C12 H3 Cl N4)'
_chemical_formula_sum            'C46 H28 Cl2 Fe2 N8 Se2'
_chemical_formula_weight         1033.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7700(12)
_cell_length_b                   9.2110(12)
_cell_length_c                   13.5822(19)
_cell_angle_alpha                89.993(3)
_cell_angle_beta                 75.599(3)
_cell_angle_gamma                71.823(3)
_cell_volume                     1006.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             514
_exptl_absorpt_coefficient_mu    2.709
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4104
_exptl_absorpt_correction_T_max  0.7734
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            7433
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4946
_reflns_number_gt                3226
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0909P)²+1.0728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4946
_refine_ls_number_parameters     282
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.6814(4) -0.0587(4) 0.7596(2) 0.0504(10) Uani 0.475(5) 1 d P A 1
Cl2 Cl 0.1565(4) 0.3391(4) 1.1252(2) 0.0699(12) Uani 0.525(5) 1 d P A 2
C1 C 0.2101(8) 0.2212(5) 0.6464(4) 0.0440(13) Uani 1 1 d . . .
C2 C 0.3667(8) 0.2447(6) 0.6158(5) 0.0508(14) Uani 1 1 d . . .
H2 H 0.4578 0.1954 0.5534 0.061 Uiso 1 1 calc R . .
C3 C 0.3727(8) 0.3471(7) 0.6913(5) 0.0540(16) Uani 1 1 d . . .
H3 H 0.4694 0.3827 0.6914 0.065 Uiso 1 1 calc R . .
C4 C 0.2193(8) 0.3911(6) 0.7661(4) 0.0493(15) Uani 1 1 d . . .
H4 H 0.1890 0.4622 0.8286 0.059 Uiso 1 1 calc R . .
C5 C 0.1160(8) 0.3139(6) 0.7386(4) 0.0431(13) Uani 1 1 d . . .
H5 H 0.0008 0.3211 0.7777 0.052 Uiso 1 1 calc R . .
C6 C 0.0422(6) 0.5419(5) 0.5226(3) 0.0309(10) Uani 1 1 d . . .
C7 C 0.2114(7) 0.5384(5) 0.4867(4) 0.0365(11) Uani 1 1 d . . .
H7 H 0.2925 0.4841 0.4217 0.044 Uiso 1 1 calc R . .
C8 C 0.2401(8) 0.6325(6) 0.5585(4) 0.0426(13) Uani 1 1 d . . .
H8 H 0.3465 0.6547 0.5526 0.051 Uiso 1 1 calc R . .
C9 C 0.0968(7) 0.6880(5) 0.6387(4) 0.0426(13) Uani 1 1 d . . .
H9 H 0.0835 0.7564 0.6996 0.051 Uiso 1 1 calc R . .
C10 C -0.0272(7) 0.6317(5) 0.6193(4) 0.0352(11) Uani 1 1 d . . .
H10 H -0.1426 0.6528 0.6638 0.042 Uiso 1 1 calc R . .
C11 C -0.0721(11) 0.1321(8) 0.6416(5) 0.076(2) Uani 1 1 d U . .
H11A H -0.0788 0.0997 0.7108 0.114 Uiso 1 1 calc R . .
H11B H -0.1258 0.0775 0.6065 0.114 Uiso 1 1 calc R . .
H11C H -0.1286 0.2427 0.6450 0.114 Uiso 1 1 calc R . .
C12 C 0.3719(6) 0.0606(5) 0.8764(3) 0.0335(10) Uani 1 1 d . A .
C13 C 0.5374(6) 0.0625(5) 0.8561(4) 0.0364(11) Uani 1 1 d . . .
H13 H 0.6182 -0.0009 0.7997 0.044 Uiso 0.525(5) 1 calc PR A 2
C14 C 0.5855(6) 0.1508(5) 0.9138(4) 0.0354(10) Uani 1 1 d . A .
H14 H 0.6983 0.1477 0.8971 0.043 Uiso 1 1 calc R . .
C15 C 0.4695(6) 0.2485(5) 0.9994(3) 0.0323(10) Uani 1 1 d . . .
C16 C 0.3025(7) 0.2477(6) 1.0192(3) 0.0366(11) Uani 1 1 d . A .
H16 H 0.2215 0.3115 1.0754 0.044 Uiso 0.475(5) 1 calc PR A 1
C17 C 0.2549(7) 0.1597(6) 0.9613(3) 0.0355(11) Uani 1 1 d . . .
H17 H 0.1418 0.1638 0.9773 0.043 Uiso 1 1 calc R A .
C18 C 0.3177(7) -0.0306(5) 0.8187(4) 0.0378(11) Uani 1 1 d . . .
C19 C 0.5236(7) 0.3371(5) 1.0576(4) 0.0376(11) Uani 1 1 d . A .
C20 C 0.1485(8) -0.0267(6) 0.8432(4) 0.0435(13) Uani 1 1 d . A .
C21 C 0.4213(9) -0.1295(7) 0.7317(5) 0.0631(19) Uani 1 1 d . A .
C22 C 0.6905(8) 0.3376(6) 1.0318(4) 0.0434(13) Uani 1 1 d . . .
C23 C 0.4216(8) 0.4380(6) 1.1443(4) 0.0466(13) Uani 1 1 d . . .
Fe1 Fe 0.18087(9) 0.45327(7) 0.62746(5) 0.0314(2) Uani 1 1 d . . .
N1 N 0.0131(8) -0.0238(7) 0.8622(4) 0.0624(15) Uani 1 1 d . . .
N2 N 0.4986(12) -0.2095(9) 0.6615(6) 0.121(3) Uani 1 1 d U . .
N3 N 0.8232(7) 0.3415(6) 1.0117(5) 0.0635(15) Uani 1 1 d . A .
N4 N 0.3456(9) 0.5219(7) 1.2138(4) 0.0747(18) Uani 1 1 d . A .
Se1 Se 0.15073(10) 0.08680(6) 0.56987(5) 0.0639(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
Cl1 C13 1.691(6) . ?
Cl2 C16 1.683(6) . ?
C1 C2 1.417(8) . ?
C1 C5 1.422(8) . ?
C1 Se1 1.886(5) . ?
C1 Fe1 2.096(5) . ?
C2 C3 1.414(8) . ?
C2 Fe1 2.071(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.410(9) . ?
C3 Fe1 2.059(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.427(8) . ?
C4 Fe1 2.045(5) . ?
C4 H4 1.0000 . ?
C5 Fe1 2.068(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.433(7) . ?
C6 C10 1.437(6) . ?
C6 C6 1.450(8) 2_566 ?
C6 Fe1 2.101(4) . ?
C7 C8 1.423(6) . ?
C7 Fe1 2.054(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.395(8) . ?
C8 Fe1 2.041(5) . ?
C8 H8 1.0000 . ?
C9 C10 1.421(7) . ?
C9 Fe1 2.047(5) . ?
C9 H9 1.0000 . ?
C10 Fe1 2.067(5) . ?
C10 H10 1.0000 . ?
C11 Se1 1.867(9) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.409(6) . ?
C12 C13 1.414(7) . ?
C12 C17 1.429(7) . ?
C13 C14 1.353(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.427(7) . ?
C14 H14 0.9500 . ?
C15 C19 1.395(6) . ?
C15 C16 1.424(7) . ?
C16 C17 1.351(6) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C21 1.414(8) . ?
C18 C20 1.426(8) . ?
C19 C23 1.417(8) . ?
C19 C22 1.419(8) . ?
C20 N1 1.143(7) . ?
C21 N2 1.131(9) . ?
C22 N3 1.139(7) . ?
C23 N4 1.139(8) . ?

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
C2 C1 C5 108.7(5) . . ?
C2 C1 Se1 122.1(4) . . ?
C5 C1 Se1 129.3(5) . . ?
C2 C1 Fe1 69.2(3) . . ?
C5 C1 Fe1 69.0(3) . . ?
Se1 C1 Fe1 127.3(2) . . ?
C3 C2 C1 107.5(6) . . ?
C3 C2 Fe1 69.5(3) . . ?
C1 C2 Fe1 71.0(3) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.6(5) . . ?
C4 C3 Fe1 69.4(3) . . ?
C2 C3 Fe1 70.4(3) . . ?
C4 C3 H3 125.7 . . ?
C2 C3 H3 125.7 . . ?
Fe1 C3 H3 125.7 . . ?
C3 C4 C5 108.3(5) . . ?
C3 C4 Fe1 70.4(3) . . ?
C5 C4 Fe1 70.6(3) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C1 C5 C4 107.0(5) . . ?
C1 C5 Fe1 71.1(3) . . ?
C4 C5 Fe1 68.8(3) . . ?
C1 C5 H5 126.5 . . ?
C4 C5 H5 126.5 . . ?
Fe1 C5 H5 126.5 . . ?
C7 C6 C10 107.6(4) . . ?
C7 C6 C6 127.3(5) . 2_566 ?
C10 C6 C6 124.7(6) . 2_566 ?
C7 C6 Fe1 68.1(2) . . ?
C10 C6 Fe1 68.5(2) . . ?
C6 C6 Fe1 123.8(4) 2_566 . ?
C8 C7 C6 107.0(4) . . ?
C8 C7 Fe1 69.2(3) . . ?
C6 C7 Fe1 71.6(3) . . ?
C8 C7 H7 126.5 . . ?
C6 C7 H7 126.5 . . ?
Fe1 C7 H7 126.5 . . ?
C9 C8 C7 109.2(4) . . ?
C9 C8 Fe1 70.3(3) . . ?
C7 C8 Fe1 70.2(3) . . ?
C9 C8 H8 125.4 . . ?
C7 C8 H8 125.4 . . ?
Fe1 C8 H8 125.4 . . ?
C8 C9 C10 108.6(4) . . ?
C8 C9 Fe1 69.8(3) . . ?
C10 C9 Fe1 70.5(3) . . ?
C8 C9 H9 125.7 . . ?
C10 C9 H9 125.7 . . ?
Fe1 C9 H9 125.7 . . ?
C9 C10 C6 107.4(5) . . ?
C9 C10 Fe1 69.1(3) . . ?
C6 C10 Fe1 71.1(3) . . ?
C9 C10 H10 126.3 . . ?
C6 C10 H10 126.3 . . ?
Fe1 C10 H10 126.3 . . ?
Se1 C11 H11A 109.5 . . ?
Se1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Se1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C12 C13 124.3(5) . . ?
C18 C12 C17 119.3(5) . . ?
C13 C12 C17 116.4(4) . . ?
C14 C13 C12 122.7(5) . . ?
C14 C13 Cl1 119.4(4) . . ?
C12 C13 Cl1 117.8(4) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
Cl1 C13 H13 3.2 . . ?
C13 C14 C15 121.1(5) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C19 C15 C16 124.3(5) . . ?
C19 C15 C14 119.6(5) . . ?
C16 C15 C14 116.1(4) . . ?
C17 C16 C15 122.6(5) . . ?
C17 C16 Cl2 115.1(4) . . ?
C15 C16 Cl2 121.9(4) . . ?
C17 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?
Cl2 C16 H16 7.6 . . ?
C16 C17 C12 121.1(5) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C12 C18 C21 124.2(5) . . ?
C12 C18 C20 121.4(5) . . ?
C21 C18 C20 114.4(5) . . ?
C15 C19 C23 125.1(5) . . ?
C15 C19 C22 121.7(5) . . ?
C23 C19 C22 113.1(4) . . ?
N1 C20 C18 179.5(6) . . ?
N2 C21 C18 177.3(9) . . ?
N3 C22 C19 178.4(6) . . ?
N4 C23 C19 176.7(6) . . ?
C8 Fe1 C4 123.2(2) . . ?
C8 Fe1 C9 39.9(2) . . ?
C4 Fe1 C9 106.2(2) . . ?
C8 Fe1 C7 40.67(18) . . ?
C4 Fe1 C7 160.5(2) . . ?
C9 Fe1 C7 68.1(2) . . ?
C8 Fe1 C3 105.5(2) . . ?
C4 Fe1 C3 40.2(3) . . ?
C9 Fe1 C3 117.7(2) . . ?
C7 Fe1 C3 124.4(2) . . ?
C8 Fe1 C10 67.6(2) . . ?
C4 Fe1 C10 120.3(2) . . ?
C9 Fe1 C10 40.40(19) . . ?
C7 Fe1 C10 68.4(2) . . ?
C3 Fe1 C10 153.1(2) . . ?
C8 Fe1 C5 161.4(2) . . ?
C4 Fe1 C5 40.6(2) . . ?
C9 Fe1 C5 126.4(2) . . ?
C7 Fe1 C5 157.33(19) . . ?
C3 Fe1 C5 67.7(2) . . ?
C10 Fe1 C5 110.1(2) . . ?
C8 Fe1 C2 119.0(3) . . ?
C4 Fe1 C2 67.7(2) . . ?
C9 Fe1 C2 152.1(2) . . ?
C7 Fe1 C2 108.0(2) . . ?
C3 Fe1 C2 40.1(2) . . ?
C10 Fe1 C2 166.2(2) . . ?
C5 Fe1 C2 67.7(2) . . ?
C8 Fe1 C1 155.0(2) . . ?
C4 Fe1 C1 67.1(2) . . ?
C9 Fe1 C1 165.0(2) . . ?
C7 Fe1 C1 122.6(2) . . ?
C3 Fe1 C1 66.7(2) . . ?
C10 Fe1 C1 130.0(2) . . ?
C5 Fe1 C1 39.9(2) . . ?
C2 Fe1 C1 39.8(2) . . ?
C8 Fe1 C6 67.30(19) . . ?
C4 Fe1 C6 156.6(2) . . ?
C9 Fe1 C6 67.44(17) . . ?
C7 Fe1 C6 40.3(2) . . ?
C3 Fe1 C6 163.1(2) . . ?
C10 Fe1 C6 40.33(17) . . ?
C5 Fe1 C6 123.8(2) . . ?
C2 Fe1 C6 128.5(2) . . ?
C1 Fe1 C6 112.93(17) . . ?
C11 Se1 C1 99.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         2.208
_refine_diff_density_min         -0.640
_refine_diff_density_rms         0.137
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1499543'
_audit_update_record             
;
2016-08-17 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Fe2 Se2, 2(C12 H3 F N4)'
_chemical_formula_sum            'C46 H28 F2 Fe2 N8 Se2'
_chemical_formula_weight         1000.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'



loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7623(9)
_cell_length_b                   9.1250(10)
_cell_length_c                   13.4315(14)
_cell_angle_alpha                90.012(2)
_cell_angle_beta                 106.064(2)
_cell_angle_gamma                107.409(2)
_cell_volume                     980.68(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    173
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             498
_exptl_absorpt_coefficient_mu    2.652
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4571
_exptl_absorpt_correction_T_max  0.8788
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            7290
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         28.31
_reflns_number_total             4807
_reflns_number_gt                3623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.5194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4807
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1132
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6555(4) 0.5482(5) 0.7185(3) 0.0383(12) Uani 0.487(5) 1 d P A 1
F2 F 0.1914(5) 0.1597(5) 0.3929(3) 0.0415(12) Uani 0.513(5) 1 d P A 2
C1 C 0.7987(4) 0.7255(3) 0.1514(2) 0.0283(6) Uani 1 1 d . . .
C2 C 0.9031(4) 0.8187(4) 0.2448(2) 0.0310(7) Uani 1 1 d . . .
H2 H 1.0202 0.8222 0.2822 0.037 Uiso 1 1 calc R . .
C3 C 0.8085(5) 0.9022(4) 0.2768(3) 0.0386(8) Uani 1 1 d . . .
H3 H 0.8475 0.9745 0.3412 0.046 Uiso 1 1 calc R . .
C4 C 0.6490(5) 0.8635(4) 0.2028(3) 0.0421(8) Uani 1 1 d . . .
H4 H 0.5559 0.9040 0.2056 0.050 Uiso 1 1 calc R . .
C5 C 0.6438(4) 0.7562(4) 0.1244(3) 0.0365(7) Uani 1 1 d . . .
H5 H 0.5469 0.7090 0.0618 0.044 Uiso 1 1 calc R . .
C6 C 0.9642(4) 1.0449(3) 0.0251(2) 0.0268(6) Uani 1 1 d . . .
C7 C 1.0427(4) 1.1352(3) 0.1237(2) 0.0322(7) Uani 1 1 d . . .
H7 H 1.1601 1.1519 0.1677 0.039 Uiso 1 1 calc R . .
C8 C 0.9267(5) 1.1972(4) 0.1474(3) 0.0401(8) Uani 1 1 d . . .
H8 H 0.9483 1.2668 0.2106 0.048 Uiso 1 1 calc R . .
C9 C 0.7743(5) 1.1456(4) 0.0661(3) 0.0393(8) Uani 1 1 d . . .
H9 H 0.6707 1.1731 0.0619 0.047 Uiso 1 1 calc R . .
C10 C 0.7948(4) 1.0486(4) -0.0084(2) 0.0318(7) Uani 1 1 d . . .
H10 H 0.7080 0.9955 -0.0742 0.038 Uiso 1 1 calc R . .
C11 C 1.0779(5) 0.6206(4) 0.1439(3) 0.0438(8) Uani 1 1 d . . .
H11A H 1.1408 0.7276 0.1387 0.066 Uiso 1 1 calc R . .
H11B H 1.1206 0.5506 0.1121 0.066 Uiso 1 1 calc R . .
H11C H 1.0910 0.6026 0.2173 0.066 Uiso 1 1 calc R . .
C12 C 0.4745(3) 0.2507(3) 0.5006(2) 0.0239(6) Uani 1 1 d . . .
C13 C 0.5910(4) 0.3541(3) 0.5863(2) 0.0271(6) Uani 1 1 d . A .
H13 H 0.7059 0.3613 0.6035 0.033 Uiso 1 1 calc R . .
C14 C 0.5409(4) 0.4419(3) 0.6435(2) 0.0267(6) Uani 1 1 d . . .
H14 H 0.6220 0.5092 0.7003 0.032 Uiso 0.513(5) 1 calc PR A 2
C15 C 0.3706(4) 0.4376(3) 0.6217(2) 0.0240(6) Uani 1 1 d . A .
C16 C 0.2527(3) 0.3329(3) 0.5355(2) 0.0251(6) Uani 1 1 d . . .
H16 H 0.1377 0.3252 0.5185 0.030 Uiso 1 1 calc R A .
C17 C 0.3034(4) 0.2456(3) 0.4786(2) 0.0248(6) Uani 1 1 d . A .
H17 H 0.2226 0.1781 0.4217 0.030 Uiso 0.487(5) 1 calc PR A 1
C18 C 0.5271(4) 0.1601(3) 0.4416(2) 0.0257(6) Uani 1 1 d . . .
C19 C 0.3189(4) 0.5292(3) 0.6806(2) 0.0265(6) Uani 1 1 d . . .
C20 C 0.4189(4) 0.0551(4) 0.3545(2) 0.0303(7) Uani 1 1 d . . .
C21 C 0.6973(4) 0.1610(3) 0.4681(2) 0.0288(6) Uani 1 1 d . . .
C22 C 0.4280(4) 0.6296(4) 0.7695(3) 0.0340(7) Uani 1 1 d . A .
C23 C 0.1483(4) 0.5244(3) 0.6555(2) 0.0282(6) Uani 1 1 d . A .
Fe1 Fe 0.83321(5) 0.96127(5) 0.13400(3) 0.02462(12) Uani 1 1 d . . .
N1 N 0.3379(4) -0.0311(4) 0.2841(2) 0.0444(7) Uani 1 1 d . . .
N2 N 0.8318(4) 0.1585(3) 0.4887(2) 0.0399(7) Uani 1 1 d . . .
N3 N 0.5108(4) 0.7111(4) 0.8410(3) 0.0581(10) Uani 1 1 d . . .
N4 N 0.0125(4) 0.5224(3) 0.6362(2) 0.0378(7) Uani 1 1 d . . .
Se1 Se 0.84397(5) 0.58331(4) 0.07186(3) 0.04066(12) 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
F1 C14 1.350(5) . ?
F2 C17 1.347(5) . ?
C1 C5 1.417(5) . ?
C1 C2 1.426(4) . ?
C1 Se1 1.877(3) . ?
C1 Fe1 2.104(3) . ?
C2 C3 1.424(5) . ?
C2 Fe1 2.063(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.415(5) . ?
C3 Fe1 2.044(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.420(5) . ?
C4 Fe1 2.054(3) . ?
C4 H4 1.0000 . ?
C5 Fe1 2.073(3) . ?
C5 H5 1.0000 . ?
C6 C6 1.436(6) 2_775 ?
C6 C7 1.437(4) . ?
C6 C10 1.437(4) . ?
C6 Fe1 2.108(3) . ?
C7 C8 1.406(5) . ?
C7 Fe1 2.075(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.419(5) . ?
C8 Fe1 2.049(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.418(5) . ?
C9 Fe1 2.046(3) . ?
C9 H9 1.0000 . ?
C10 Fe1 2.053(3) . ?
C10 H10 1.0000 . ?
C11 Se1 1.934(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C18 1.397(4) . ?
C12 C13 1.426(4) . ?
C12 C17 1.432(4) . ?
C13 C14 1.350(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.428(4) . ?
C14 H14 0.9500 . ?
C15 C19 1.398(4) . ?
C15 C16 1.438(4) . ?
C16 C17 1.348(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C20 1.424(4) . ?
C18 C21 1.432(4) . ?
C19 C22 1.422(4) . ?
C19 C23 1.426(4) . ?
C20 N1 1.145(4) . ?
C21 N2 1.140(4) . ?
C22 N3 1.138(4) . ?
C23 N4 1.139(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C2 108.1(3) . . ?
C5 C1 Se1 122.7(2) . . ?
C2 C1 Se1 129.2(2) . . ?
C5 C1 Fe1 69.00(18) . . ?
C2 C1 Fe1 68.46(17) . . ?
Se1 C1 Fe1 128.25(15) . . ?
C3 C2 C1 107.5(3) . . ?
C3 C2 Fe1 68.98(18) . . ?
C1 C2 Fe1 71.52(17) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.3(3) . . ?
C4 C3 Fe1 70.19(19) . . ?
C2 C3 Fe1 70.45(17) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C3 C4 C5 108.0(3) . . ?
C3 C4 Fe1 69.4(2) . . ?
C5 C4 Fe1 70.60(19) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
Fe1 C4 H4 126.0 . . ?
C1 C5 C4 108.1(3) . . ?
C1 C5 Fe1 71.34(18) . . ?
C4 C5 Fe1 69.2(2) . . ?
C1 C5 H5 125.9 . . ?
C4 C5 H5 125.9 . . ?
Fe1 C5 H5 125.9 . . ?
C6 C6 C7 126.4(4) 2_775 . ?
C6 C6 C10 126.4(4) 2_775 . ?
C7 C6 C10 106.9(3) . . ?
C6 C6 Fe1 123.9(3) 2_775 . ?
C7 C6 Fe1 68.67(17) . . ?
C10 C6 Fe1 67.73(17) . . ?
C8 C7 C6 108.3(3) . . ?
C8 C7 Fe1 69.1(2) . . ?
C6 C7 Fe1 71.17(18) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
Fe1 C7 H7 125.8 . . ?
C7 C8 C9 108.6(3) . . ?
C7 C8 Fe1 71.04(18) . . ?
C9 C8 Fe1 69.60(19) . . ?
C7 C8 H8 125.7 . . ?
C9 C8 H8 125.7 . . ?
Fe1 C8 H8 125.7 . . ?
C10 C9 C8 108.1(3) . . ?
C10 C9 Fe1 70.02(17) . . ?
C8 C9 Fe1 69.86(18) . . ?
C10 C9 H9 125.9 . . ?
C8 C9 H9 125.9 . . ?
Fe1 C9 H9 125.9 . . ?
C9 C10 C6 108.0(3) . . ?
C9 C10 Fe1 69.50(18) . . ?
C6 C10 Fe1 71.88(17) . . ?
C9 C10 H10 126.0 . . ?
C6 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
Se1 C11 H11A 109.5 . . ?
Se1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
Se1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C12 C13 120.8(3) . . ?
C18 C12 C17 122.5(3) . . ?
C13 C12 C17 116.7(3) . . ?
C14 C13 C12 121.1(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
F1 C14 C13 119.8(3) . . ?
F1 C14 C15 117.5(3) . . ?
C13 C14 C15 122.4(3) . . ?
F1 C14 H14 5.3 . . ?
C13 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C19 C15 C14 122.4(3) . . ?
C19 C15 C16 121.0(3) . . ?
C14 C15 C16 116.5(3) . . ?
C17 C16 C15 120.8(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
F2 C17 C16 118.7(3) . . ?
F2 C17 C12 118.6(3) . . ?
C16 C17 C12 122.4(3) . . ?
F2 C17 H17 4.8 . . ?
C16 C17 H17 118.8 . . ?
C12 C17 H17 118.8 . . ?
C12 C18 C20 124.3(3) . . ?
C12 C18 C21 121.6(3) . . ?
C20 C18 C21 114.1(3) . . ?
C15 C19 C22 123.6(3) . . ?
C15 C19 C23 121.0(3) . . ?
C22 C19 C23 115.3(3) . . ?
N1 C20 C18 177.0(3) . . ?
N2 C21 C18 178.6(3) . . ?
N3 C22 C19 177.7(4) . . ?
N4 C23 C19 179.1(4) . . ?
C3 Fe1 C9 123.38(14) . . ?
C3 Fe1 C8 105.87(14) . . ?
C9 Fe1 C8 40.54(15) . . ?
C3 Fe1 C10 160.96(14) . . ?
C9 Fe1 C10 40.48(13) . . ?
C8 Fe1 C10 68.11(14) . . ?
C3 Fe1 C4 40.40(15) . . ?
C9 Fe1 C4 105.35(15) . . ?
C8 Fe1 C4 117.55(15) . . ?
C10 Fe1 C4 124.86(15) . . ?
C3 Fe1 C2 40.57(13) . . ?
C9 Fe1 C2 161.58(14) . . ?
C8 Fe1 C2 125.83(14) . . ?
C10 Fe1 C2 157.25(13) . . ?
C4 Fe1 C2 67.94(14) . . ?
C3 Fe1 C5 67.73(15) . . ?
C9 Fe1 C5 119.14(15) . . ?
C8 Fe1 C5 152.59(15) . . ?
C10 Fe1 C5 108.80(14) . . ?
C4 Fe1 C5 40.24(14) . . ?
C2 Fe1 C5 67.61(13) . . ?
C3 Fe1 C7 119.71(14) . . ?
C9 Fe1 C7 67.65(14) . . ?
C8 Fe1 C7 39.86(14) . . ?
C10 Fe1 C7 68.03(13) . . ?
C4 Fe1 C7 152.53(14) . . ?
C2 Fe1 C7 109.88(13) . . ?
C5 Fe1 C7 166.48(14) . . ?
C3 Fe1 C1 67.29(13) . . ?
C9 Fe1 C1 154.93(14) . . ?
C8 Fe1 C1 164.44(14) . . ?
C10 Fe1 C1 122.86(12) . . ?
C4 Fe1 C1 67.04(13) . . ?
C2 Fe1 C1 40.02(12) . . ?
C5 Fe1 C1 39.65(13) . . ?
C7 Fe1 C1 130.05(13) . . ?
C3 Fe1 C6 155.74(14) . . ?
C9 Fe1 C6 67.54(13) . . ?
C8 Fe1 C6 67.30(13) . . ?
C10 Fe1 C6 40.39(12) . . ?
C4 Fe1 C6 163.74(14) . . ?
C2 Fe1 C6 123.26(12) . . ?
C5 Fe1 C6 129.07(13) . . ?
C7 Fe1 C6 40.16(12) . . ?
C1 Fe1 C6 112.81(11) . . ?
C1 Se1 C11 99.43(15) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.103
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
