# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Philippe Schollhammer'
_publ_contact_author_email       SCHOLLHA@UNIV-BREST.FR

_publ_section_title              
;
Absence of terminal hydride upon protonation of
dissymetrically disubstituted di-iron azadithiolate models of the
[FeFe]H2ases active site
;
_publ_requested_category         FM
loop_
_publ_author_name
'Philippe Schollhammer'
'Jean-Francois Capon'
'Salah Ezzaher'
'Frederic Gloaguen'
'Pierre-Yves Orain'
;
F.Petillon
;
'Thierry Roisnel'
'Jean Talarmin'

# Attachment '2-new.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2007-12-25 at 15:32:11
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:\wingx\files\archive.dat
# CIF files read : ipr-phen import

data_ipr-phen
_database_code_depnum_ccdc_archive 'CCDC 675690'

_audit_creation_date             2007-12-25T15:32:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            iPr-phen
_chemical_formula_moiety         'C21 H19 Fe2 N3 O4 S2'
_chemical_formula_sum            'C21 H19 Fe2 N3 O4 S2'
_chemical_formula_weight         553.21
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4906(13)
_cell_length_b                   10.2311(15)
_cell_length_c                   12.8702(19)
_cell_angle_alpha                67.315(7)
_cell_angle_beta                 89.583(8)
_cell_angle_gamma                73.043(8)
_cell_volume                     1095.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7420
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      27.66
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             564
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.55
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_T_max  0.969

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_type       'by SAINT Bruker-AXS'
_diffrn_orient_matrix_ub_11      0.0562442
_diffrn_orient_matrix_ub_12      0.0636068
_diffrn_orient_matrix_ub_13      -0.0502828
_diffrn_orient_matrix_ub_21      -0.0728583
_diffrn_orient_matrix_ub_22      0.0281339
_diffrn_orient_matrix_ub_23      -0.0667078
_diffrn_orient_matrix_ub_31      -0.0619495
_diffrn_orient_matrix_ub_32      0.0872062
_diffrn_orient_matrix_ub_33      0.014693
_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_number            16375
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_reflns_number_total             4963
_reflns_number_gt                4198
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SMART, 2006'
_computing_cell_refinement       'Bruker SMART, 2006'
_computing_data_reduction        'Bruker SAINT, 2006'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0237P)^2^+2.5635P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         4963
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.096

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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 0.19206(5) 0.64468(5) 0.29585(4) 0.01642(13) Uani 1 1 d . . .
Fe2 Fe 0.23101(6) 0.39159(5) 0.29039(5) 0.01993(14) Uani 1 1 d . . .
S1 S 0.18157(9) 0.60143(9) 0.13722(8) 0.01847(18) Uani 1 1 d . . .
S2 S 0.03281(9) 0.50941(10) 0.34770(7) 0.01921(19) Uani 1 1 d . . .
O1 O 0.0929(3) 0.2295(3) 0.2040(2) 0.0349(7) Uani 1 1 d . . .
O2 O -0.0075(3) 0.9510(3) 0.2393(3) 0.0435(8) Uani 1 1 d . . .
O3 O 0.4775(3) 0.6899(3) 0.2365(2) 0.0317(6) Uani 1 1 d . . .
O4 O 0.3064(3) 0.5334(3) 0.5353(2) 0.0293(6) Uani 1 1 d . . .
N1 N 0.4426(3) 0.3321(3) 0.2641(3) 0.0283(8) Uani 1 1 d . . .
N2 N 0.3168(4) 0.2554(3) 0.4488(3) 0.0306(8) Uani 1 1 d . . .
N3 N -0.1180(3) 0.7183(3) 0.1395(2) 0.0184(6) Uani 1 1 d . . .
C1 C 0.1546(4) 0.2870(4) 0.2412(3) 0.0242(8) Uani 1 1 d . . .
C2 C 0.0689(4) 0.8321(4) 0.2593(3) 0.0253(8) Uani 1 1 d . . .
C3 C 0.3646(4) 0.6745(4) 0.2597(3) 0.0210(7) Uani 1 1 d . . .
C4 C 0.2576(4) 0.5787(4) 0.4422(3) 0.0206(7) Uani 1 1 d . . .
C5 C -0.0108(4) 0.6692(4) 0.0720(3) 0.0216(7) Uani 1 1 d . . .
C6 C -0.1289(4) 0.5942(4) 0.2400(3) 0.0207(7) Uani 1 1 d . . .
C7 C -0.2651(4) 0.8182(4) 0.0741(3) 0.0236(8) Uani 1 1 d . . .
C8 C -0.2529(5) 0.9678(4) -0.0081(4) 0.0368(10) Uani 1 1 d . . .
C9 C -0.3395(4) 0.7493(5) 0.0133(3) 0.0312(9) Uani 1 1 d . . .
C10 C 0.5037(4) 0.3634(5) 0.1670(4) 0.0355(10) Uani 1 1 d . . .
C11 C 0.6571(5) 0.3195(5) 0.1630(6) 0.0532(15) Uani 1 1 d . . .
C12 C 0.7521(5) 0.2421(6) 0.2619(7) 0.064(2) Uani 1 1 d . . .
C13 C 0.6924(5) 0.2070(5) 0.3642(6) 0.0583(18) Uani 1 1 d . . .
C14 C 0.7790(7) 0.1221(7) 0.4742(8) 0.086(3) Uani 1 1 d . . .
C15 C 0.7151(8) 0.0808(6) 0.5693(8) 0.084(3) Uani 1 1 d . . .
C16 C 0.5559(7) 0.1190(5) 0.5691(5) 0.0575(18) Uani 1 1 d . . .
C17 C 0.4814(8) 0.0740(5) 0.6626(5) 0.068(2) Uani 1 1 d . . .
C18 C 0.3298(7) 0.1157(5) 0.6499(4) 0.0561(17) Uani 1 1 d . . .
C19 C 0.2498(6) 0.2075(4) 0.5419(4) 0.0410(12) Uani 1 1 d . . .
C20 C 0.4685(5) 0.2091(4) 0.4627(4) 0.0413(13) Uani 1 1 d . . .
C21 C 0.5370(5) 0.2515(4) 0.3621(5) 0.0379(12) Uani 1 1 d . . .
H5A H -0.0212 0.7515 -0.0008 0.026 Uiso 1 1 calc R . .
H5B H -0.0325 0.59 0.0582 0.026 Uiso 1 1 calc R . .
H6A H -0.1428 0.5182 0.2174 0.025 Uiso 1 1 calc R . .
H6B H -0.2162 0.6286 0.2737 0.025 Uiso 1 1 calc R . .
H7 H -0.3305 0.8386 0.129 0.028 Uiso 1 1 calc R . .
H8A H -0.2073 1.0094 0.0324 0.055 Uiso 1 1 calc R . .
H8B H -0.3502 1.0349 -0.0427 0.055 Uiso 1 1 calc R . .
H8C H -0.1935 0.9534 -0.0658 0.055 Uiso 1 1 calc R . .
H9A H -0.2766 0.7233 -0.039 0.047 Uiso 1 1 calc R . .
H9B H -0.4328 0.82 -0.0273 0.047 Uiso 1 1 calc R . .
H9C H -0.356 0.6614 0.068 0.047 Uiso 1 1 calc R . .
H10 H 0.4414 0.4169 0.099 0.043 Uiso 1 1 calc R . .
H11 H 0.6946 0.3426 0.0934 0.064 Uiso 1 1 calc R . .
H12 H 0.8543 0.2139 0.2605 0.077 Uiso 1 1 calc R . .
H14 H 0.8819 0.0954 0.479 0.103 Uiso 1 1 calc R . .
H15 H 0.7753 0.0254 0.6382 0.101 Uiso 1 1 calc R . .
H17 H 0.5343 0.0154 0.7342 0.081 Uiso 1 1 calc R . .
H18 H 0.2797 0.0835 0.7124 0.067 Uiso 1 1 calc R . .
H19 H 0.1467 0.236 0.5349 0.049 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Fe1 0.0141(2) 0.0143(2) 0.0216(3) -0.0072(2) 0.00065(18) -0.00542(18)
Fe2 0.0176(3) 0.0137(2) 0.0277(3) -0.0077(2) -0.0055(2) -0.00441(19)
S1 0.0138(4) 0.0171(4) 0.0249(5) -0.0099(4) 0.0026(3) -0.0033(3)
S2 0.0189(4) 0.0192(4) 0.0189(4) -0.0044(3) -0.0010(3) -0.0093(3)
O1 0.0506(19) 0.0373(17) 0.0265(15) -0.0095(13) -0.0020(13) -0.0319(15)
O2 0.0349(17) 0.0212(15) 0.073(2) -0.0247(16) -0.0118(16) 0.0013(13)
O3 0.0253(14) 0.0380(16) 0.0324(16) -0.0084(13) 0.0052(12) -0.0189(13)
O4 0.0315(15) 0.0306(15) 0.0278(15) -0.0110(12) -0.0004(12) -0.0136(12)
N1 0.0149(14) 0.0180(15) 0.055(2) -0.0223(16) -0.0066(15) 0.0007(12)
N2 0.041(2) 0.0118(14) 0.036(2) -0.0084(14) -0.0172(16) -0.0061(14)
N3 0.0149(14) 0.0179(14) 0.0194(15) -0.0050(12) 0.0034(11) -0.0043(11)
C1 0.0275(19) 0.0186(17) 0.0218(19) -0.0023(15) -0.0033(15) -0.0085(15)
C2 0.0217(18) 0.0225(19) 0.037(2) -0.0140(17) -0.0002(16) -0.0112(15)
C3 0.0239(18) 0.0164(17) 0.0201(18) -0.0028(14) -0.0026(14) -0.0087(14)
C4 0.0190(17) 0.0169(16) 0.028(2) -0.0094(15) 0.0023(15) -0.0082(14)
C5 0.0161(16) 0.0229(18) 0.0246(19) -0.0104(15) 0.0001(14) -0.0032(14)
C6 0.0189(17) 0.0233(18) 0.0193(18) -0.0042(15) -0.0005(13) -0.0116(14)
C7 0.0166(17) 0.0254(19) 0.0221(19) -0.0073(15) 0.0037(14) 0.0000(14)
C8 0.032(2) 0.022(2) 0.038(2) 0.0003(18) 0.0040(18) 0.0018(17)
C9 0.0166(18) 0.047(3) 0.028(2) -0.0142(19) 0.0014(15) -0.0095(17)
C10 0.0188(19) 0.025(2) 0.071(3) -0.027(2) 0.006(2) -0.0070(16)
C11 0.021(2) 0.036(3) 0.121(5) -0.050(3) 0.017(3) -0.0096(19)
C12 0.012(2) 0.042(3) 0.158(7) -0.068(4) -0.004(3) 0.004(2)
C13 0.023(2) 0.028(2) 0.130(5) -0.052(3) -0.033(3) 0.0116(19)
C14 0.044(3) 0.035(3) 0.174(8) -0.061(5) -0.066(5) 0.023(3)
C15 0.080(5) 0.022(3) 0.133(7) -0.033(4) -0.085(5) 0.015(3)
C16 0.077(4) 0.0092(19) 0.073(4) -0.012(2) -0.055(3) 0.001(2)
C17 0.112(5) 0.012(2) 0.060(4) 0.000(2) -0.067(4) -0.010(3)
C18 0.109(5) 0.019(2) 0.036(3) 0.0015(19) -0.034(3) -0.029(3)
C19 0.069(3) 0.019(2) 0.033(2) -0.0043(18) -0.021(2) -0.018(2)
C20 0.044(3) 0.0090(17) 0.065(3) -0.016(2) -0.034(2) 0.0036(17)
C21 0.028(2) 0.0169(18) 0.073(3) -0.027(2) -0.017(2) 0.0018(16)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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 1.778(4) . ?
Fe1 C4 1.784(4) . ?
Fe1 C2 1.808(4) . ?
Fe1 S1 2.2582(11) . ?
Fe1 S2 2.2667(10) . ?
Fe1 Fe2 2.5354(8) . ?
Fe2 C1 1.747(4) . ?
Fe2 N2 1.983(3) . ?
Fe2 N1 1.989(3) . ?
Fe2 S1 2.2084(11) . ?
Fe2 S2 2.2087(11) . ?
S2 C6 1.832(3) . ?
S1 C5 1.832(3) . ?
O1 C1 1.159(4) . ?
O4 C4 1.148(4) . ?
N3 C5 1.437(4) . ?
N3 C6 1.451(4) . ?
N3 C7 1.491(4) . ?
O2 C2 1.148(5) . ?
O3 C3 1.149(4) . ?
N1 C10 1.337(6) . ?
N1 C21 1.363(5) . ?
C15 C14 1.335(11) . ?
C15 C16 1.446(10) . ?
C15 H15 0.93 . ?
C7 C9 1.526(6) . ?
C7 C8 1.527(5) . ?
C7 H7 0.98 . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
N2 C19 1.341(6) . ?
N2 C20 1.368(6) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C13 C12 1.388(9) . ?
C13 C21 1.408(6) . ?
C13 C14 1.444(9) . ?
C10 C11 1.400(5) . ?
C10 H10 0.93 . ?
C11 C12 1.372(8) . ?
C11 H11 0.93 . ?
C17 C18 1.368(9) . ?
C17 C16 1.382(9) . ?
C17 H17 0.93 . ?
C19 C18 1.408(6) . ?
C19 H19 0.93 . ?
C18 H18 0.93 . ?
C14 H14 0.93 . ?
C16 C20 1.418(6) . ?
C21 C20 1.416(7) . ?
C12 H12 0.93 . ?

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 C4 89.39(16) . . ?
C3 Fe1 C2 102.58(16) . . ?
C4 Fe1 C2 104.95(17) . . ?
C3 Fe1 S1 86.49(12) . . ?
C4 Fe1 S1 149.48(12) . . ?
C2 Fe1 S1 105.47(13) . . ?
C3 Fe1 S2 155.35(12) . . ?
C4 Fe1 S2 88.59(11) . . ?
C2 Fe1 S2 101.68(12) . . ?
S1 Fe1 S2 82.89(4) . . ?
C3 Fe1 Fe2 101.54(12) . . ?
C4 Fe1 Fe2 97.05(11) . . ?
C2 Fe1 Fe2 147.29(11) . . ?
S1 Fe1 Fe2 54.49(3) . . ?
S2 Fe1 Fe2 54.42(3) . . ?
C1 Fe2 N2 104.46(15) . . ?
C1 Fe2 N1 103.44(16) . . ?
N2 Fe2 N1 81.79(16) . . ?
C1 Fe2 S1 100.68(12) . . ?
N2 Fe2 S1 154.83(9) . . ?
N1 Fe2 S1 91.13(11) . . ?
C1 Fe2 S2 99.76(13) . . ?
N2 Fe2 S2 91.68(11) . . ?
N1 Fe2 S2 156.79(10) . . ?
S1 Fe2 S2 85.38(4) . . ?
C1 Fe2 Fe1 145.23(12) . . ?
N2 Fe2 Fe1 101.55(9) . . ?
N1 Fe2 Fe1 102.76(9) . . ?
S1 Fe2 Fe1 56.35(3) . . ?
S2 Fe2 Fe1 56.58(3) . . ?
C6 S2 Fe2 111.87(13) . . ?
C6 S2 Fe1 109.73(11) . . ?
Fe2 S2 Fe1 69.00(3) . . ?
C5 S1 Fe2 112.83(12) . . ?
C5 S1 Fe1 110.21(12) . . ?
Fe2 S1 Fe1 69.16(3) . . ?
C5 N3 C6 111.6(3) . . ?
C5 N3 C7 114.0(3) . . ?
C6 N3 C7 113.0(3) . . ?
C10 N1 C21 117.0(4) . . ?
C10 N1 Fe2 130.0(3) . . ?
C21 N1 Fe2 113.0(3) . . ?
C14 C15 C16 122.5(6) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
N3 C7 C9 114.2(3) . . ?
N3 C7 C8 110.6(3) . . ?
C9 C7 C8 111.2(3) . . ?
N3 C7 H7 106.8 . . ?
C9 C7 H7 106.8 . . ?
C8 C7 H7 106.8 . . ?
N3 C6 S2 114.3(2) . . ?
N3 C6 H6A 108.7 . . ?
S2 C6 H6A 108.7 . . ?
N3 C6 H6B 108.7 . . ?
S2 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
O4 C4 Fe1 176.8(3) . . ?
C19 N2 C20 116.9(4) . . ?
C19 N2 Fe2 130.3(3) . . ?
C20 N2 Fe2 112.8(3) . . ?
O3 C3 Fe1 178.1(3) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C1 Fe2 173.7(3) . . ?
N3 C5 S1 113.9(2) . . ?
N3 C5 H5A 108.8 . . ?
S1 C5 H5A 108.8 . . ?
N3 C5 H5B 108.8 . . ?
S1 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C13 C21 118.6(5) . . ?
C12 C13 C14 124.4(6) . . ?
C21 C13 C14 116.9(7) . . ?
N1 C10 C11 123.1(5) . . ?
N1 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 119.8(6) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C18 C17 C16 119.9(4) . . ?
C18 C17 H17 120 . . ?
C16 C17 H17 120 . . ?
N2 C19 C18 122.4(5) . . ?
N2 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
O2 C2 Fe1 177.8(4) . . ?
C17 C18 C19 119.9(6) . . ?
C17 C18 H18 120 . . ?
C19 C18 H18 120 . . ?
C15 C14 C13 121.7(6) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C17 C16 C20 117.2(5) . . ?
C17 C16 C15 126.1(5) . . ?
C20 C16 C15 116.8(7) . . ?
N1 C21 C13 122.8(5) . . ?
N1 C21 C20 115.5(4) . . ?
C13 C21 C20 121.6(5) . . ?
N2 C20 C21 115.9(4) . . ?
N2 C20 C16 123.7(5) . . ?
C21 C20 C16 120.4(5) . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 Fe1 Fe2 C1 -132.5(3) . . . . ?
C4 Fe1 Fe2 C1 136.7(3) . . . . ?
C2 Fe1 Fe2 C1 4.4(3) . . . . ?
S1 Fe1 Fe2 C1 -55.3(2) . . . . ?
S2 Fe1 Fe2 C1 53.5(2) . . . . ?
C3 Fe1 Fe2 N2 89.67(16) . . . . ?
C4 Fe1 Fe2 N2 -1.15(16) . . . . ?
C2 Fe1 Fe2 N2 -133.5(3) . . . . ?
S1 Fe1 Fe2 N2 166.81(12) . . . . ?
S2 Fe1 Fe2 N2 -84.31(12) . . . . ?
C3 Fe1 Fe2 N1 5.58(16) . . . . ?
C4 Fe1 Fe2 N1 -85.23(16) . . . . ?
C2 Fe1 Fe2 N1 142.4(3) . . . . ?
S1 Fe1 Fe2 N1 82.73(11) . . . . ?
S2 Fe1 Fe2 N1 -168.40(11) . . . . ?
C3 Fe1 Fe2 S1 -77.15(12) . . . . ?
C4 Fe1 Fe2 S1 -167.97(12) . . . . ?
C2 Fe1 Fe2 S1 59.7(2) . . . . ?
S2 Fe1 Fe2 S1 108.87(4) . . . . ?
C3 Fe1 Fe2 S2 173.98(12) . . . . ?
C4 Fe1 Fe2 S2 83.16(12) . . . . ?
C2 Fe1 Fe2 S2 -49.2(2) . . . . ?
S1 Fe1 Fe2 S2 -108.87(4) . . . . ?
C1 Fe2 S2 C6 -48.64(17) . . . . ?
N2 Fe2 S2 C6 -153.62(15) . . . . ?
N1 Fe2 S2 C6 133.5(3) . . . . ?
S1 Fe2 S2 C6 51.42(12) . . . . ?
Fe1 Fe2 S2 C6 103.63(12) . . . . ?
C1 Fe2 S2 Fe1 -152.27(12) . . . . ?
N2 Fe2 S2 Fe1 102.75(9) . . . . ?
N1 Fe2 S2 Fe1 29.8(3) . . . . ?
S1 Fe2 S2 Fe1 -52.21(3) . . . . ?
C3 Fe1 S2 C6 -120.9(3) . . . . ?
C4 Fe1 S2 C6 153.66(18) . . . . ?
C2 Fe1 S2 C6 48.69(19) . . . . ?
S1 Fe1 S2 C6 -55.71(14) . . . . ?
Fe2 Fe1 S2 C6 -106.63(14) . . . . ?
C3 Fe1 S2 Fe2 -14.3(3) . . . . ?
C4 Fe1 S2 Fe2 -99.71(12) . . . . ?
C2 Fe1 S2 Fe2 155.32(13) . . . . ?
S1 Fe1 S2 Fe2 50.92(3) . . . . ?
C1 Fe2 S1 C5 47.56(19) . . . . ?
N2 Fe2 S1 C5 -135.6(3) . . . . ?
N1 Fe2 S1 C5 151.46(16) . . . . ?
S2 Fe2 S1 C5 -51.53(13) . . . . ?
Fe1 Fe2 S1 C5 -103.93(13) . . . . ?
C1 Fe2 S1 Fe1 151.49(14) . . . . ?
N2 Fe2 S1 Fe1 -31.7(3) . . . . ?
N1 Fe2 S1 Fe1 -104.61(9) . . . . ?
S2 Fe2 S1 Fe1 52.41(3) . . . . ?
C3 Fe1 S1 C5 -145.55(17) . . . . ?
C4 Fe1 S1 C5 131.6(3) . . . . ?
C2 Fe1 S1 C5 -43.46(18) . . . . ?
S2 Fe1 S1 C5 56.74(13) . . . . ?
Fe2 Fe1 S1 C5 107.59(13) . . . . ?
C3 Fe1 S1 Fe2 106.85(11) . . . . ?
C4 Fe1 S1 Fe2 24.0(2) . . . . ?
C2 Fe1 S1 Fe2 -151.05(12) . . . . ?
S2 Fe1 S1 Fe2 -50.85(3) . . . . ?
C1 Fe2 N1 C10 71.0(4) . . . . ?
N2 Fe2 N1 C10 173.9(3) . . . . ?
S1 Fe2 N1 C10 -30.3(3) . . . . ?
S2 Fe2 N1 C10 -111.2(4) . . . . ?
Fe1 Fe2 N1 C10 -86.0(3) . . . . ?
C1 Fe2 N1 C21 -111.6(3) . . . . ?
N2 Fe2 N1 C21 -8.6(2) . . . . ?
S1 Fe2 N1 C21 147.1(2) . . . . ?
S2 Fe2 N1 C21 66.3(4) . . . . ?
Fe1 Fe2 N1 C21 91.5(2) . . . . ?
C5 N3 C7 C9 58.2(4) . . . . ?
C6 N3 C7 C9 -70.5(4) . . . . ?
C5 N3 C7 C8 -68.0(4) . . . . ?
C6 N3 C7 C8 163.2(3) . . . . ?
C5 N3 C6 S2 70.8(3) . . . . ?
C7 N3 C6 S2 -159.1(3) . . . . ?
Fe2 S2 C6 N3 -68.5(3) . . . . ?
Fe1 S2 C6 N3 6.0(3) . . . . ?
C1 Fe2 N2 C19 -72.2(4) . . . . ?
N1 Fe2 N2 C19 -174.0(3) . . . . ?
S1 Fe2 N2 C19 111.0(4) . . . . ?
S2 Fe2 N2 C19 28.3(3) . . . . ?
Fe1 Fe2 N2 C19 84.5(3) . . . . ?
C1 Fe2 N2 C20 110.1(3) . . . . ?
N1 Fe2 N2 C20 8.3(2) . . . . ?
S1 Fe2 N2 C20 -66.7(4) . . . . ?
S2 Fe2 N2 C20 -149.4(2) . . . . ?
Fe1 Fe2 N2 C20 -93.2(2) . . . . ?
C6 N3 C5 S1 -69.8(3) . . . . ?
C7 N3 C5 S1 160.7(2) . . . . ?
Fe2 S1 C5 N3 67.8(3) . . . . ?
Fe1 S1 C5 N3 -7.4(3) . . . . ?
C21 N1 C10 C11 -1.0(6) . . . . ?
Fe2 N1 C10 C11 176.3(3) . . . . ?
N1 C10 C11 C12 -0.9(6) . . . . ?
C20 N2 C19 C18 1.0(5) . . . . ?
Fe2 N2 C19 C18 -176.7(3) . . . . ?
C16 C17 C18 C19 -1.6(7) . . . . ?
N2 C19 C18 C17 0.9(6) . . . . ?
C16 C15 C14 C13 -0.6(9) . . . . ?
C12 C13 C14 C15 -174.2(5) . . . . ?
C21 C13 C14 C15 3.4(8) . . . . ?
C18 C17 C16 C20 0.5(6) . . . . ?
C18 C17 C16 C15 -178.5(4) . . . . ?
C14 C15 C16 C17 176.3(5) . . . . ?
C14 C15 C16 C20 -2.7(8) . . . . ?
C10 N1 C21 C13 2.6(5) . . . . ?
Fe2 N1 C21 C13 -175.2(3) . . . . ?
C10 N1 C21 C20 -174.7(3) . . . . ?
Fe2 N1 C21 C20 7.5(4) . . . . ?
C12 C13 C21 N1 -2.3(6) . . . . ?
C14 C13 C21 N1 179.9(4) . . . . ?
C12 C13 C21 C20 174.9(4) . . . . ?
C14 C13 C21 C20 -2.9(6) . . . . ?
C19 N2 C20 C21 175.3(3) . . . . ?
Fe2 N2 C20 C21 -6.6(4) . . . . ?
C19 N2 C20 C16 -2.2(5) . . . . ?
Fe2 N2 C20 C16 175.9(3) . . . . ?
N1 C21 C20 N2 -0.6(5) . . . . ?
C13 C21 C20 N2 -177.9(3) . . . . ?
N1 C21 C20 C16 177.0(3) . . . . ?
C13 C21 C20 C16 -0.4(6) . . . . ?
C17 C16 C20 N2 1.5(6) . . . . ?
C15 C16 C20 N2 -179.5(4) . . . . ?
C17 C16 C20 C21 -175.9(4) . . . . ?
C15 C16 C20 C21 3.1(6) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C21 C13 C12 C11 0.3(6) . . . . ?
C14 C13 C12 C11 177.9(4) . . . . ?