# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_feiitacnbenz

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H31 Fe N5 O2, 2(C F3 O3 S)'
_chemical_formula_sum            'C19 H31 F6 Fe N5 O8 S2'
_chemical_formula_weight         691.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.1902(6)
_cell_length_b                   15.4925(5)
_cell_length_c                   22.7717(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5711.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5840
_cell_measurement_theta_min      3.8730
_cell_measurement_theta_max      74.9760

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_F_000             2848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.069
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    6.436
_shelx_estimated_absorpt_T_min   0.666
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6191
_exptl_absorpt_correction_T_max  0.7540
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker, 2012) Additional spherical absorption correction applied with mu*r =  0.2000 Lambda/2 correction factor = 0.0000'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   micro-source
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\f scans and \w scans with \k offset'
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_reflns_number            21092
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.882
_diffrn_reflns_theta_max         76.721
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5935
_reflns_number_gt                4747
_reflns_threshold_expression     'I > 2\s(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
'CrystaMaker (CrystalMaker Software ltd., 2012)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+6.1265P]
 where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5935
_refine_ls_number_parameters     375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1078
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Fe1 Fe 0.45590(3) 0.38677(3) 0.29831(2) 0.02455(12) Uani 1 1 d . . . . .
O1 O 0.53039(13) 0.47635(14) 0.34406(9) 0.0369(5) Uani 1 1 d . . . . .
H1A H 0.5080 0.5263 0.3431 0.055 Uiso 1 1 d R U . . .
H1B H 0.5781 0.4791 0.3276 0.055 Uiso 1 1 d R U . . .
O2 O 0.36743(13) 0.48748(13) 0.28267(9) 0.0346(5) Uani 1 1 d . . . . .
H2A H 0.3664 0.5220 0.3121 0.052 Uiso 1 1 d R U . . .
H2B H 0.3664 0.5104 0.2434 0.052 Uiso 1 1 d R U . . .
N1 N 0.49006(15) 0.40130(14) 0.20845(10) 0.0263(5) Uani 1 1 d . . . . .
N2 N 0.37952(15) 0.28595(14) 0.25258(10) 0.0280(5) Uani 1 1 d . . . . .
N3 N 0.38600(15) 0.33349(15) 0.37361(10) 0.0304(5) Uani 1 1 d . . . . .
N4 N 0.53129(15) 0.27053(15) 0.31826(11) 0.0299(5) Uani 1 1 d . . . . .
N5 N 0.45551(15) 0.38171(15) 0.11470(10) 0.0302(5) Uani 1 1 d . . . . .
C1 C 0.54626(17) 0.44513(17) 0.17364(12) 0.0265(6) Uani 1 1 d . . . . .
C2 C 0.61577(19) 0.49235(18) 0.18903(14) 0.0317(6) Uani 1 1 d . . . . .
H2 H 0.6313 0.4997 0.2290 0.038 Uiso 1 1 calc R U . . .
C3 C 0.66164(19) 0.52827(19) 0.14399(15) 0.0369(7) Uani 1 1 d . . . . .
H3 H 0.7090 0.5618 0.1533 0.044 Uiso 1 1 calc R U . . .
C4 C 0.6402(2) 0.5166(2) 0.08535(15) 0.0412(7) Uani 1 1 d . . . . .
H4 H 0.6734 0.5422 0.0557 0.049 Uiso 1 1 calc R U . . .
C5 C 0.5717(2) 0.4686(2) 0.06912(14) 0.0382(7) Uani 1 1 d . . . . .
H5 H 0.5573 0.4601 0.0291 0.046 Uiso 1 1 calc R U . . .
C6 C 0.52516(19) 0.43349(18) 0.11446(13) 0.0302(6) Uani 1 1 d . . . . .
C7 C 0.4121(2) 0.3481(2) 0.06380(14) 0.0478(9) Uani 1 1 d . . . . .
H7A H 0.4324 0.3769 0.0283 0.072 Uiso 1 1 calc R U . . .
H7B H 0.3528 0.3588 0.0681 0.072 Uiso 1 1 calc R U . . .
H7C H 0.4220 0.2858 0.0606 0.072 Uiso 1 1 calc R U . . .
C8 C 0.43735(18) 0.36505(17) 0.17165(12) 0.0271(6) Uani 1 1 d . . . . .
C9 C 0.36376(19) 0.3161(2) 0.19244(13) 0.0325(6) Uani 1 1 d . . . . .
H9A H 0.3144 0.3537 0.1918 0.039 Uiso 1 1 calc R U . . .
H9B H 0.3535 0.2662 0.1663 0.039 Uiso 1 1 calc R U . . .
C10 C 0.30262(18) 0.2822(2) 0.28809(14) 0.0352(7) Uani 1 1 d . . . . .
H10A H 0.2682 0.2333 0.2746 0.042 Uiso 1 1 calc R U . . .
H10B H 0.2707 0.3360 0.2824 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3225(2) 0.2710(2) 0.35284(14) 0.0373(7) Uani 1 1 d . . . . .
H11A H 0.2713 0.2788 0.3761 0.045 Uiso 1 1 calc R U . . .
H11B H 0.3426 0.2115 0.3596 0.045 Uiso 1 1 calc R U . . .
C12 C 0.3464(2) 0.4023(2) 0.40889(14) 0.0408(7) Uani 1 1 d . . . . .
H12A H 0.3878 0.4457 0.4196 0.061 Uiso 1 1 calc R U . . .
H12B H 0.3227 0.3772 0.4446 0.061 Uiso 1 1 calc R U . . .
H12C H 0.3026 0.4297 0.3858 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4507(2) 0.2909(2) 0.40945(13) 0.0359(7) Uani 1 1 d . . . . .
H13A H 0.4242 0.2590 0.4421 0.043 Uiso 1 1 calc R U . . .
H13B H 0.4871 0.3355 0.4268 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5023(2) 0.2290(2) 0.37332(14) 0.0357(7) Uani 1 1 d . . . . .
H14A H 0.5505 0.2099 0.3967 0.043 Uiso 1 1 calc R U . . .
H14B H 0.4689 0.1774 0.3636 0.043 Uiso 1 1 calc R U . . .
C15 C 0.62007(19) 0.2926(2) 0.32227(15) 0.0384(7) Uani 1 1 d . . . . .
H15A H 0.6360 0.3272 0.2881 0.058 Uiso 1 1 calc R U . . .
H15B H 0.6529 0.2395 0.3231 0.058 Uiso 1 1 calc R U . . .
H15C H 0.6301 0.3258 0.3582 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5175(2) 0.21468(19) 0.26633(13) 0.0342(6) Uani 1 1 d . . . . .
H16A H 0.5427 0.1574 0.2735 0.041 Uiso 1 1 calc R U . . .
H16B H 0.5452 0.2406 0.2318 0.041 Uiso 1 1 calc R U . . .
C17 C 0.4266(2) 0.20312(18) 0.25287(14) 0.0342(6) Uani 1 1 d . . . . .
H17A H 0.4209 0.1752 0.2140 0.041 Uiso 1 1 calc R U . . .
H17B H 0.4021 0.1640 0.2825 0.041 Uiso 1 1 calc R U . . .
S1 S 0.24595(4) 0.44749(5) 0.65515(3) 0.03020(16) Uani 1 1 d . . . . .
F1 F 0.2225(2) 0.4761(3) 0.54477(12) 0.1190(13) Uani 1 1 d . . . . .
F2 F 0.32772(17) 0.4004(2) 0.56268(12) 0.0900(9) Uani 1 1 d . . . . .
F3 F 0.2068(2) 0.3459(2) 0.56914(14) 0.1160(14) Uani 1 1 d . . . . .
O3 O 0.15992(13) 0.46310(15) 0.66575(10) 0.0430(5) Uani 1 1 d . . . . .
O4 O 0.29721(16) 0.52265(16) 0.65780(13) 0.0553(7) Uani 1 1 d . . . . .
O5 O 0.27798(18) 0.37423(17) 0.68529(13) 0.0598(7) Uani 1 1 d . . . . .
C18 C 0.2498(3) 0.4156(3) 0.57873(16) 0.0586(10) Uani 1 1 d . . . . .
S2 S 0.40089(5) 0.67285(5) 0.38780(3) 0.03625(18) Uani 1 1 d . . . . .
F4 F 0.3827(3) 0.59625(19) 0.48869(12) 0.1037(12) Uani 1 1 d . . . . .
F5 F 0.29089(16) 0.69358(18) 0.47085(10) 0.0696(7) Uani 1 1 d . . . . .
F6 F 0.41432(19) 0.7298(2) 0.49498(12) 0.0908(10) Uani 1 1 d . . . . .
O6 O 0.34192(15) 0.61591(14) 0.36152(10) 0.0443(6) Uani 1 1 d . . . . .
O7 O 0.39134(17) 0.76100(15) 0.37107(13) 0.0557(7) Uani 1 1 d . . . . .
O8 O 0.48373(17) 0.63998(19) 0.38762(14) 0.0636(8) Uani 1 1 d . . . . .
C19 C 0.3700(3) 0.6727(3) 0.46456(16) 0.0576(10) Uani 1 1 d . . . . .

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 0.0273(2) 0.0249(2) 0.0215(2) 0.00082(16) -0.00051(16) -0.00117(17)
O1 0.0331(11) 0.0367(11) 0.0411(12) -0.0103(9) -0.0018(9) -0.0020(9)
O2 0.0414(12) 0.0359(11) 0.0265(10) -0.0027(9) -0.0017(9) 0.0095(9)
N1 0.0317(12) 0.0242(11) 0.0229(11) 0.0013(9) 0.0016(9) -0.0002(9)
N2 0.0300(12) 0.0287(12) 0.0254(11) 0.0011(10) -0.0025(9) -0.0043(10)
N3 0.0326(12) 0.0347(13) 0.0238(11) 0.0027(10) 0.0023(9) 0.0010(10)
N4 0.0297(12) 0.0296(12) 0.0304(12) 0.0032(10) -0.0013(10) 0.0012(10)
N5 0.0358(13) 0.0321(12) 0.0226(12) 0.0009(10) -0.0027(10) 0.0024(10)
C1 0.0305(14) 0.0221(13) 0.0270(13) -0.0003(11) 0.0033(11) 0.0016(11)
C2 0.0352(15) 0.0261(14) 0.0339(15) -0.0001(12) 0.0009(12) 0.0023(12)
C3 0.0316(15) 0.0294(15) 0.0498(19) 0.0046(14) 0.0067(14) 0.0032(12)
C4 0.0415(17) 0.0402(17) 0.0420(18) 0.0093(14) 0.0141(14) 0.0056(14)
C5 0.0486(18) 0.0369(16) 0.0291(15) 0.0063(13) 0.0055(14) 0.0056(14)
C6 0.0354(15) 0.0275(14) 0.0278(14) 0.0011(11) 0.0021(12) 0.0031(12)
C7 0.061(2) 0.057(2) 0.0252(15) -0.0035(15) -0.0106(15) -0.0049(18)
C8 0.0322(14) 0.0251(13) 0.0240(13) -0.0001(10) -0.0025(11) 0.0013(11)
C9 0.0361(15) 0.0346(15) 0.0268(14) 0.0003(12) -0.0059(12) -0.0071(13)
C10 0.0285(14) 0.0394(17) 0.0376(16) 0.0020(13) 0.0009(12) -0.0071(12)
C11 0.0337(15) 0.0418(17) 0.0364(16) 0.0048(13) 0.0052(13) -0.0077(13)
C12 0.0443(18) 0.0480(18) 0.0300(16) -0.0026(14) 0.0098(14) 0.0062(15)
C13 0.0415(17) 0.0414(16) 0.0248(14) 0.0086(13) -0.0008(12) 0.0023(14)
C14 0.0390(16) 0.0350(16) 0.0332(16) 0.0076(12) -0.0032(13) 0.0032(13)
C15 0.0292(15) 0.0421(17) 0.0440(18) 0.0013(14) -0.0037(13) 0.0034(13)
C16 0.0412(16) 0.0288(14) 0.0325(15) -0.0014(12) 0.0007(13) 0.0059(13)
C17 0.0444(17) 0.0256(14) 0.0325(15) -0.0011(12) 0.0001(13) -0.0021(13)
S1 0.0302(3) 0.0331(3) 0.0273(3) -0.0031(3) -0.0018(3) 0.0017(3)
F1 0.120(3) 0.195(4) 0.0425(14) 0.040(2) -0.0120(16) 0.021(3)
F2 0.0636(16) 0.146(3) 0.0599(16) -0.0353(17) 0.0258(13) -0.0042(17)
F3 0.109(2) 0.152(3) 0.087(2) -0.080(2) 0.0293(18) -0.066(2)
O3 0.0303(11) 0.0544(14) 0.0444(13) -0.0083(11) 0.0019(10) 0.0030(10)
O4 0.0460(14) 0.0476(14) 0.0723(18) -0.0155(13) 0.0033(13) -0.0121(11)
O5 0.0587(16) 0.0566(16) 0.0642(17) 0.0203(13) -0.0025(14) 0.0191(13)
C18 0.054(2) 0.091(3) 0.0314(17) -0.0077(19) 0.0025(17) -0.008(2)
S2 0.0346(4) 0.0352(4) 0.0390(4) -0.0083(3) -0.0002(3) -0.0022(3)
F4 0.172(4) 0.0902(19) 0.0494(15) 0.0236(14) 0.0064(18) 0.045(2)
F5 0.0686(16) 0.1012(19) 0.0391(12) -0.0055(12) 0.0131(11) 0.0115(14)
F6 0.093(2) 0.120(2) 0.0597(16) -0.0475(16) -0.0397(15) 0.0344(18)
O6 0.0459(13) 0.0434(12) 0.0436(13) -0.0160(10) 0.0022(11) -0.0084(10)
O7 0.0619(16) 0.0348(12) 0.0703(18) -0.0011(12) 0.0133(14) -0.0032(12)
O8 0.0398(14) 0.0698(17) 0.081(2) -0.0286(15) -0.0079(14) 0.0123(13)
C19 0.070(3) 0.067(2) 0.0358(19) -0.0071(18) -0.0142(18) 0.022(2)

_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 O1 2.113(2) . yes
Fe1 N1 2.132(2) . yes
Fe1 O2 2.148(2) . yes
Fe1 N3 2.214(2) . yes
Fe1 N4 2.222(2) . yes
Fe1 N2 2.248(2) . yes
O1 H1A 0.8550 . ?
O1 H1B 0.8594 . ?
O2 H2A 0.8578 . ?
O2 H2B 0.9628 . ?
N1 C8 1.321(4) . ?
N1 C1 1.385(4) . ?
N2 C9 1.469(4) . ?
N2 C10 1.486(4) . ?
N2 C17 1.493(4) . ?
N3 C12 1.481(4) . ?
N3 C13 1.482(4) . ?
N3 C11 1.490(4) . ?
N4 C15 1.480(4) . ?
N4 C16 1.482(4) . ?
N4 C14 1.485(4) . ?
N5 C8 1.355(4) . ?
N5 C6 1.384(4) . ?
N5 C7 1.452(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.490(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.519(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.515(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.513(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
S1 O5 1.424(2) . ?
S1 O4 1.431(3) . ?
S1 O3 1.434(2) . ?
S1 C18 1.810(4) . ?
F1 C18 1.293(5) . ?
F2 C18 1.334(5) . ?
F3 C18 1.303(5) . ?
S2 O7 1.426(3) . ?
S2 O6 1.431(2) . ?
S2 O8 1.435(3) . ?
S2 C19 1.818(4) . ?
F4 C19 1.321(5) . ?
F5 C19 1.329(5) . ?
F6 C19 1.333(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 N1 104.83(9) . . ?
O1 Fe1 O2 89.16(8) . . ?
N1 Fe1 O2 86.40(8) . . ?
O1 Fe1 N3 98.90(9) . . ?
N1 Fe1 N3 156.27(9) . . ?
O2 Fe1 N3 93.34(9) . . ?
O1 Fe1 N4 96.77(9) . . ?
N1 Fe1 N4 98.01(9) . . ?
O2 Fe1 N4 171.42(9) . . ?
N3 Fe1 N4 79.65(9) . . ?
O1 Fe1 N2 176.99(9) . . ?
N1 Fe1 N2 76.79(9) . . ?
O2 Fe1 N2 93.50(8) . . ?
N3 Fe1 N2 79.54(9) . . ?
N4 Fe1 N2 80.43(9) . . ?
Fe1 O1 H1A 109.9 . . ?
Fe1 O1 H1B 109.3 . . ?
H1A O1 H1B 109.0 . . ?
Fe1 O2 H2A 109.6 . . ?
Fe1 O2 H2B 115.7 . . ?
H2A O2 H2B 119.8 . . ?
C8 N1 C1 105.7(2) . . ?
C8 N1 Fe1 113.35(19) . . ?
C1 N1 Fe1 140.51(19) . . ?
C9 N2 C10 112.0(2) . . ?
C9 N2 C17 111.5(2) . . ?
C10 N2 C17 113.1(2) . . ?
C9 N2 Fe1 107.84(16) . . ?
C10 N2 Fe1 103.67(17) . . ?
C17 N2 Fe1 108.30(17) . . ?
C12 N3 C13 109.1(2) . . ?
C12 N3 C11 110.0(2) . . ?
C13 N3 C11 111.9(2) . . ?
C12 N3 Fe1 111.88(18) . . ?
C13 N3 Fe1 103.37(17) . . ?
C11 N3 Fe1 110.46(17) . . ?
C15 N4 C16 109.3(2) . . ?
C15 N4 C14 110.8(2) . . ?
C16 N4 C14 111.9(2) . . ?
C15 N4 Fe1 111.01(18) . . ?
C16 N4 Fe1 103.11(17) . . ?
C14 N4 Fe1 110.47(18) . . ?
C8 N5 C6 106.9(2) . . ?
C8 N5 C7 126.2(3) . . ?
C6 N5 C7 126.8(3) . . ?
N1 C1 C2 130.3(3) . . ?
N1 C1 C6 109.1(2) . . ?
C2 C1 C6 120.6(3) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.7(3) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 116.5(3) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
N5 C6 C5 132.2(3) . . ?
N5 C6 C1 105.6(2) . . ?
C5 C6 C1 122.1(3) . . ?
N5 C7 H7A 109.5 . . ?
N5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 N5 112.7(3) . . ?
N1 C8 C9 122.1(3) . . ?
N5 C8 C9 125.1(3) . . ?
N2 C9 C8 108.6(2) . . ?
N2 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N2 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C11 110.8(2) . . ?
N2 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N3 C11 C10 112.3(2) . . ?
N3 C11 H11A 109.1 . . ?
C10 C11 H11A 109.1 . . ?
N3 C11 H11B 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C13 C14 111.8(2) . . ?
N3 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N3 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N4 C14 C13 111.0(2) . . ?
N4 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N4 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 C17 112.2(2) . . ?
N4 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N4 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 113.3(2) . . ?
N2 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
O5 S1 O4 114.64(18) . . ?
O5 S1 O3 114.02(16) . . ?
O4 S1 O3 114.76(15) . . ?
O5 S1 C18 103.5(2) . . ?
O4 S1 C18 104.04(19) . . ?
O3 S1 C18 103.99(17) . . ?
F1 C18 F3 108.5(4) . . ?
F1 C18 F2 106.6(4) . . ?
F3 C18 F2 108.3(4) . . ?
F1 C18 S1 111.4(3) . . ?
F3 C18 S1 111.7(3) . . ?
F2 C18 S1 110.1(3) . . ?
O7 S2 O6 113.97(17) . . ?
O7 S2 O8 116.13(18) . . ?
O6 S2 O8 113.81(15) . . ?
O7 S2 C19 103.20(18) . . ?
O6 S2 C19 102.58(18) . . ?
O8 S2 C19 105.04(19) . . ?
F4 C19 F5 108.8(4) . . ?
F4 C19 F6 107.2(3) . . ?
F5 C19 F6 107.5(3) . . ?
F4 C19 S2 111.0(3) . . ?
F5 C19 S2 111.6(3) . . ?
F6 C19 S2 110.5(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1B O4 0.86 2.05 2.791(3) 144.7 5_666 yes
O1 H1A O8 0.85 2.07 2.825(3) 147.0 . yes
O2 H2B O3 0.96 1.86 2.805(3) 165.1 2_564 yes
O2 H2A O6 0.86 1.88 2.712(3) 162.5 . yes

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.065
_database_code_depnum_ccdc_archive 'CCDC 960138'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mm2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H27 F6 Fe N5 O6 S2'
_chemical_formula_sum            'C19 H27 F6 Fe N5 O6 S2'
_chemical_formula_weight         655.43
_chemical_absolute_configuration ad

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'
O O 0.0106 0.0060 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7786(15)
_cell_length_b                   15.903(3)
_cell_length_c                   17.253(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2682.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1698
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      16.38

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.784032
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS v2.10 BRUKER 2001'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            41111
_diffrn_reflns_av_R_equivalents  0.2045
_diffrn_reflns_av_sigmaI/netI    0.1616
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.50
_reflns_number_total             6172
_reflns_number_gt                3204
_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 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^)+(0.0568P)^2^+0.0000P] 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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_number_reflns         6172
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2014
_refine_ls_R_factor_gt           0.1130
_refine_ls_wR_factor_ref         0.1883
_refine_ls_wR_factor_gt          0.1598
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe -0.73276(11) -0.01145(7) -0.23929(6) 0.0326(3) Uani 1 1 d . . .
S1 S -0.8349(3) -0.20779(17) -0.17587(17) 0.0562(8) Uani 1 1 d . . .
O1 O -0.7838(7) -0.1247(4) -0.1870(4) 0.066(2) Uani 1 1 d . . .
N1 N -0.5979(7) -0.0444(5) -0.3317(4) 0.0391(19) Uani 1 1 d . . .
C1 C -0.5458(9) -0.1107(6) -0.3738(5) 0.041(2) Uani 1 1 d . . .
F1 F -0.7210(11) -0.2111(6) -0.0418(5) 0.143(3) Uani 1 1 d . . .
S2 S -0.4342(3) -0.0074(2) -0.12254(17) 0.0638(8) Uani 1 1 d . . .
N2 N -0.4216(7) 0.0010(5) -0.4037(4) 0.048(2) Uani 1 1 d . . .
O2 O -0.7479(12) -0.2724(5) -0.1981(5) 0.114(3) Uani 1 1 d . . .
C2 C -0.5909(10) -0.1943(6) -0.3799(6) 0.051(3) Uani 1 1 d . . .
H2A H -0.6670 -0.2140 -0.3508 0.061 Uiso 1 1 calc R . .
F2 F -0.9163(11) -0.1558(5) -0.0405(5) 0.142(4) Uani 1 1 d . . .
N3 N -0.6833(8) 0.1133(5) -0.2896(4) 0.048(2) Uani 1 1 d . . .
O3 O -0.9726(9) -0.2168(6) -0.1977(6) 0.116(3) Uani 1 1 d . . .
F3 F -0.8946(9) -0.2893(5) -0.0516(4) 0.121(3) Uani 1 1 d . . .
C3 C -0.5207(12) -0.2468(6) -0.4294(6) 0.060(3) Uani 1 1 d . . .
H3A H -0.5484 -0.3038 -0.4346 0.073 Uiso 1 1 calc R . .
O4 O -0.5592(6) -0.0023(5) -0.1635(3) 0.0609(18) Uani 1 1 d . . .
N4 N -0.9162(7) 0.0056(5) -0.3116(4) 0.052(2) Uani 1 1 d . . .
F4 F -0.2459(9) -0.1222(5) -0.1168(4) 0.135(3) Uani 1 1 d . . .
C4 C -0.4089(12) -0.2170(8) -0.4723(7) 0.071(4) Uani 1 1 d . . .
H4A H -0.3614 -0.2546 -0.5056 0.086 Uiso 1 1 calc R . .
C5 C -0.3667(11) -0.1358(7) -0.4675(6) 0.060(3) Uani 1 1 d . . .
H5A H -0.2917 -0.1156 -0.4971 0.072 Uiso 1 1 calc R . .
N5 N -0.8519(7) 0.0713(5) -0.1606(4) 0.0421(19) Uani 1 1 d . . .
O5 O -0.4490(10) -0.0145(9) -0.0409(5) 0.169(6) Uani 1 1 d . . .
F5 F -0.4420(10) -0.1666(5) -0.1441(9) 0.193(6) Uani 1 1 d . . .
F6 F -0.3283(9) -0.1014(6) -0.2250(5) 0.143(3) Uani 1 1 d . . .
O6 O -0.3409(10) 0.0508(6) -0.1450(9) 0.168(6) Uani 1 1 d . . .
C6 C -0.4375(10) -0.0847(7) -0.4181(5) 0.048(3) Uani 1 1 d . . .
C7 C -0.3237(11) 0.0574(7) -0.4368(6) 0.073(3) Uani 1 1 d . . .
H7A H -0.2554 0.0252 -0.4659 0.109 Uiso 1 1 calc R . .
H7B H -0.2783 0.0890 -0.3954 0.109 Uiso 1 1 calc R . .
H7C H -0.3703 0.0966 -0.4718 0.109 Uiso 1 1 calc R . .
C8 C -0.5222(8) 0.0201(6) -0.3515(5) 0.040(2) Uani 1 1 d . . .
C9 C -0.5416(10) 0.1080(6) -0.3198(6) 0.052(3) Uani 1 1 d . . .
H9A H -0.4751 0.1191 -0.2777 0.063 Uiso 1 1 calc R . .
H9B H -0.5275 0.1502 -0.3612 0.063 Uiso 1 1 calc R . .
C10 C -0.7824(11) 0.1329(7) -0.3515(5) 0.062(3) Uani 1 1 d . . .
H10A H -0.7321 0.1548 -0.3970 0.075 Uiso 1 1 calc R . .
H10B H -0.8444 0.1779 -0.3332 0.075 Uiso 1 1 calc R . .
C11 C -0.8663(12) 0.0589(7) -0.3762(6) 0.067(3) Uani 1 1 d . . .
H11A H -0.9462 0.0795 -0.4059 0.080 Uiso 1 1 calc R . .
H11B H -0.8108 0.0237 -0.4115 0.080 Uiso 1 1 calc R . .
C12 C -0.9678(11) -0.0733(7) -0.3463(6) 0.067(3) Uani 1 1 d . . .
H12A H -1.0412 -0.0603 -0.3831 0.101 Uiso 1 1 calc R . .
H12B H -1.0032 -0.1099 -0.3053 0.101 Uiso 1 1 calc R . .
H12C H -0.8931 -0.1018 -0.3735 0.101 Uiso 1 1 calc R . .
C13 C -1.0236(10) 0.0482(7) -0.2651(7) 0.077(3) Uani 1 1 d . . .
H13A H -1.0329 0.1070 -0.2833 0.092 Uiso 1 1 calc R . .
H13B H -1.1121 0.0196 -0.2739 0.092 Uiso 1 1 calc R . .
C14 C -0.9941(10) 0.0485(7) -0.1822(6) 0.065(3) Uani 1 1 d . . .
H14A H -1.0140 -0.0082 -0.1612 0.078 Uiso 1 1 calc R . .
H14B H -1.0572 0.0885 -0.1566 0.078 Uiso 1 1 calc R . .
C15 C -0.8249(11) 0.0523(6) -0.0771(5) 0.066(3) Uani 1 1 d . . .
H15A H -0.8899 0.0834 -0.0447 0.099 Uiso 1 1 calc R . .
H15B H -0.7314 0.0693 -0.0638 0.099 Uiso 1 1 calc R . .
H15C H -0.8357 -0.0082 -0.0680 0.099 Uiso 1 1 calc R . .
C16 C -0.8233(11) 0.1599(7) -0.1783(6) 0.063(3) Uani 1 1 d . . .
H16A H -0.8165 0.1917 -0.1292 0.075 Uiso 1 1 calc R . .
H16B H -0.9008 0.1834 -0.2083 0.075 Uiso 1 1 calc R . .
C17 C -0.6946(12) 0.1717(6) -0.2234(6) 0.070(3) Uani 1 1 d . . .
H17A H -0.6910 0.2302 -0.2429 0.084 Uiso 1 1 calc R . .
H17B H -0.6154 0.1632 -0.1886 0.084 Uiso 1 1 calc R . .
C18 C -0.8427(16) -0.2140(9) -0.0716(8) 0.083(4) Uani 1 1 d . . .
C19 C -0.3625(15) -0.1077(10) -0.1481(8) 0.087(4) Uani 1 1 d . . .

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 0.0307(6) 0.0364(6) 0.0308(6) 0.0033(6) 0.0017(5) 0.0005(5)
S1 0.070(2) 0.0400(16) 0.0591(18) 0.0089(14) 0.0003(16) -0.0121(15)
O1 0.072(5) 0.059(4) 0.066(5) 0.012(4) 0.003(4) -0.018(4)
N1 0.035(4) 0.044(5) 0.039(5) -0.011(4) 0.004(4) 0.000(4)
C1 0.039(6) 0.058(7) 0.025(5) -0.002(5) -0.007(5) 0.014(5)
F1 0.132(8) 0.206(10) 0.090(6) 0.021(6) -0.026(6) -0.028(7)
S2 0.0418(15) 0.066(2) 0.084(2) -0.0110(18) -0.0169(14) 0.0054(17)
N2 0.049(5) 0.062(6) 0.033(4) -0.002(4) 0.013(3) 0.015(5)
O2 0.172(9) 0.069(5) 0.102(6) 0.005(4) 0.056(7) 0.025(7)
C2 0.053(7) 0.053(7) 0.047(6) 0.001(5) -0.006(5) 0.006(5)
F2 0.223(11) 0.100(6) 0.102(6) 0.000(5) 0.086(7) 0.032(7)
N3 0.052(5) 0.059(5) 0.034(4) -0.001(4) 0.008(4) 0.009(4)
O3 0.093(7) 0.127(8) 0.128(8) 0.036(6) -0.047(6) -0.064(6)
F3 0.164(8) 0.109(6) 0.091(6) 0.052(5) 0.033(5) -0.004(6)
C3 0.085(9) 0.037(6) 0.059(8) -0.002(6) -0.023(7) 0.003(6)
O4 0.044(4) 0.079(5) 0.060(4) -0.001(4) -0.018(3) 0.014(4)
N4 0.054(5) 0.057(5) 0.045(5) -0.004(5) -0.014(4) 0.007(5)
F4 0.114(7) 0.171(7) 0.120(6) -0.028(5) -0.036(6) 0.108(6)
C4 0.076(9) 0.075(9) 0.062(8) -0.025(7) 0.005(7) 0.031(7)
C5 0.058(7) 0.075(8) 0.047(7) 0.003(6) -0.004(6) 0.031(6)
N5 0.039(5) 0.045(5) 0.043(5) -0.001(4) 0.008(4) 0.008(4)
O5 0.163(10) 0.298(15) 0.045(5) -0.033(8) -0.031(5) 0.119(11)
F5 0.128(9) 0.062(6) 0.390(19) 0.005(8) 0.020(10) -0.014(5)
F6 0.156(8) 0.178(9) 0.094(6) -0.037(6) 0.008(6) 0.062(7)
O6 0.072(7) 0.090(8) 0.342(19) -0.012(9) 0.015(9) -0.006(6)
C6 0.046(6) 0.066(7) 0.032(6) 0.007(5) -0.006(5) 0.026(6)
C7 0.055(8) 0.096(9) 0.067(8) 0.020(6) 0.011(6) 0.001(6)
C8 0.025(5) 0.055(6) 0.041(5) -0.008(5) -0.002(4) -0.005(5)
C9 0.056(7) 0.053(6) 0.048(6) 0.008(5) 0.009(6) -0.006(5)
C10 0.066(7) 0.077(8) 0.045(6) 0.021(5) 0.007(6) 0.015(6)
C11 0.097(9) 0.071(8) 0.034(6) 0.002(6) -0.032(6) 0.011(7)
C12 0.070(8) 0.068(8) 0.065(8) 0.004(6) -0.027(6) -0.002(6)
C13 0.038(6) 0.098(9) 0.095(10) -0.032(8) -0.001(7) 0.012(5)
C14 0.040(6) 0.087(9) 0.067(8) 0.002(7) 0.025(6) 0.014(6)
C15 0.078(8) 0.078(8) 0.042(7) 0.006(5) 0.018(6) 0.011(6)
C16 0.079(8) 0.060(7) 0.049(7) -0.006(6) 0.017(6) 0.004(6)
C17 0.090(9) 0.054(6) 0.065(8) -0.008(6) 0.016(7) 0.000(6)
C18 0.093(11) 0.078(10) 0.078(10) 0.030(8) 0.010(9) -0.001(9)
C19 0.079(11) 0.118(13) 0.066(10) -0.022(8) -0.004(8) 0.032(9)

_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 O1 2.076(6) . ?
Fe1 N1 2.134(7) . ?
Fe1 O4 2.147(5) . ?
Fe1 N4 2.202(7) . ?
Fe1 N3 2.219(8) . ?
Fe1 N5 2.221(7) . ?
S1 O2 1.388(8) . ?
S1 O3 1.405(8) . ?
S1 O1 1.425(6) . ?
S1 C18 1.803(13) . ?
N1 C8 1.310(11) . ?
N1 C1 1.379(10) . ?
C1 C6 1.370(12) . ?
C1 C2 1.405(12) . ?
F1 C18 1.298(14) . ?
S2 O6 1.356(10) . ?
S2 O4 1.414(5) . ?
S2 O5 1.421(9) . ?
S2 C19 1.798(13) . ?
N2 C8 1.367(10) . ?
N2 C6 1.394(12) . ?
N2 C7 1.431(12) . ?
C2 C3 1.378(13) . ?
C2 H2A 0.9500 . ?
F2 C18 1.290(14) . ?
N3 C17 1.475(12) . ?
N3 C10 1.475(11) . ?
N3 C9 1.483(11) . ?
F3 C18 1.345(13) . ?
C3 C4 1.403(14) . ?
C3 H3A 0.9500 . ?
N4 C12 1.478(12) . ?
N4 C11 1.483(12) . ?
N4 C13 1.485(12) . ?
F4 C19 1.282(13) . ?
C4 C5 1.358(14) . ?
C4 H4A 0.9500 . ?
C5 C6 1.366(13) . ?
C5 H5A 0.9500 . ?
N5 C16 1.468(12) . ?
N5 C14 1.484(12) . ?
N5 C15 1.497(11) . ?
F5 C19 1.218(15) . ?
F6 C19 1.372(14) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.514(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.497(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.460(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.491(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 N1 105.1(3) . . ?
O1 Fe1 O4 89.1(3) . . ?
N1 Fe1 O4 89.0(3) . . ?
O1 Fe1 N4 99.1(3) . . ?
N1 Fe1 N4 96.3(3) . . ?
O4 Fe1 N4 168.7(3) . . ?
O1 Fe1 N3 176.8(3) . . ?
N1 Fe1 N3 78.0(3) . . ?
O4 Fe1 N3 90.3(3) . . ?
N4 Fe1 N3 81.1(3) . . ?
O1 Fe1 N5 97.0(3) . . ?
N1 Fe1 N5 157.8(3) . . ?
O4 Fe1 N5 90.2(3) . . ?
N4 Fe1 N5 81.1(3) . . ?
N3 Fe1 N5 79.8(3) . . ?
O2 S1 O3 116.0(7) . . ?
O2 S1 O1 115.7(5) . . ?
O3 S1 O1 113.2(5) . . ?
O2 S1 C18 105.1(6) . . ?
O3 S1 C18 102.8(7) . . ?
O1 S1 C18 101.5(6) . . ?
S1 O1 Fe1 161.3(5) . . ?
C8 N1 C1 104.6(8) . . ?
C8 N1 Fe1 110.7(6) . . ?
C1 N1 Fe1 144.1(7) . . ?
C6 C1 N1 110.4(9) . . ?
C6 C1 C2 119.2(9) . . ?
N1 C1 C2 130.3(9) . . ?
O6 S2 O4 113.6(7) . . ?
O6 S2 O5 114.0(9) . . ?
O4 S2 O5 114.4(5) . . ?
O6 S2 C19 105.8(7) . . ?
O4 S2 C19 105.3(6) . . ?
O5 S2 C19 102.2(7) . . ?
C8 N2 C6 104.7(8) . . ?
C8 N2 C7 127.3(9) . . ?
C6 N2 C7 128.0(8) . . ?
C3 C2 C1 117.5(10) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C17 N3 C10 112.2(7) . . ?
C17 N3 C9 112.2(8) . . ?
C10 N3 C9 111.8(7) . . ?
C17 N3 Fe1 104.1(5) . . ?
C10 N3 Fe1 109.2(6) . . ?
C9 N3 Fe1 106.9(5) . . ?
C2 C3 C4 120.8(10) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
S2 O4 Fe1 169.6(5) . . ?
C12 N4 C11 107.0(8) . . ?
C12 N4 C13 111.4(8) . . ?
C11 N4 C13 112.2(8) . . ?
C12 N4 Fe1 113.8(6) . . ?
C11 N4 Fe1 103.2(6) . . ?
C13 N4 Fe1 109.0(6) . . ?
C5 C4 C3 121.7(10) . . ?
C5 C4 H4A 119.2 . . ?
C3 C4 H4A 119.2 . . ?
C4 C5 C6 116.8(11) . . ?
C4 C5 H5A 121.6 . . ?
C6 C5 H5A 121.6 . . ?
C16 N5 C14 111.2(8) . . ?
C16 N5 C15 111.1(8) . . ?
C14 N5 C15 110.9(8) . . ?
C16 N5 Fe1 110.0(5) . . ?
C14 N5 Fe1 101.2(6) . . ?
C15 N5 Fe1 112.1(6) . . ?
C5 C6 C1 124.0(10) . . ?
C5 C6 N2 129.6(10) . . ?
C1 C6 N2 106.4(9) . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 N2 113.9(8) . . ?
N1 C8 C9 123.9(8) . . ?
N2 C8 C9 122.2(9) . . ?
N3 C9 C8 107.3(7) . . ?
N3 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
N3 C9 H9B 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
N3 C10 C11 113.6(8) . . ?
N3 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N3 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N4 C11 C10 114.6(8) . . ?
N4 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
N4 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N4 113.1(9) . . ?
C14 C13 H13A 109.0 . . ?
N4 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
N4 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 N5 115.5(8) . . ?
C13 C14 H14A 108.4 . . ?
N5 C14 H14A 108.4 . . ?
C13 C14 H14B 108.4 . . ?
N5 C14 H14B 108.4 . . ?
H14A C14 H14B 107.5 . . ?
N5 C15 H15A 109.5 . . ?
N5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 C17 113.0(9) . . ?
N5 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
N5 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N3 C17 C16 112.8(9) . . ?
N3 C17 H17A 109.0 . . ?
C16 C17 H17A 109.0 . . ?
N3 C17 H17B 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
F2 C18 F1 108.7(14) . . ?
F2 C18 F3 108.7(12) . . ?
F1 C18 F3 106.0(11) . . ?
F2 C18 S1 113.5(10) . . ?
F1 C18 S1 110.8(10) . . ?
F3 C18 S1 108.8(10) . . ?
F5 C19 F4 113.9(15) . . ?
F5 C19 F6 105.5(13) . . ?
F4 C19 F6 101.7(11) . . ?
F5 C19 S2 114.8(11) . . ?
F4 C19 S2 113.8(10) . . ?
F6 C19 S2 105.5(10) . . ?

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
O2 S1 O1 Fe1 82.9(16) . . . . ?
O3 S1 O1 Fe1 -54.5(17) . . . . ?
C18 S1 O1 Fe1 -163.9(16) . . . . ?
N1 Fe1 O1 S1 -59.6(16) . . . . ?
O4 Fe1 O1 S1 -148.3(16) . . . . ?
N4 Fe1 O1 S1 39.5(16) . . . . ?
N3 Fe1 O1 S1 133(5) . . . . ?
N5 Fe1 O1 S1 121.6(16) . . . . ?
O1 Fe1 N1 C8 -157.8(6) . . . . ?
O4 Fe1 N1 C8 -69.0(6) . . . . ?
N4 Fe1 N1 C8 101.0(6) . . . . ?
N3 Fe1 N1 C8 21.5(6) . . . . ?
N5 Fe1 N1 C8 19.0(11) . . . . ?
O1 Fe1 N1 C1 10.5(11) . . . . ?
O4 Fe1 N1 C1 99.3(10) . . . . ?
N4 Fe1 N1 C1 -90.6(10) . . . . ?
N3 Fe1 N1 C1 -170.2(10) . . . . ?
N5 Fe1 N1 C1 -172.7(8) . . . . ?
C8 N1 C1 C6 0.7(10) . . . . ?
Fe1 N1 C1 C6 -168.1(7) . . . . ?
C8 N1 C1 C2 -175.8(9) . . . . ?
Fe1 N1 C1 C2 15.5(17) . . . . ?
C6 C1 C2 C3 1.4(13) . . . . ?
N1 C1 C2 C3 177.6(9) . . . . ?
O1 Fe1 N3 C17 17(6) . . . . ?
N1 Fe1 N3 C17 -150.9(6) . . . . ?
O4 Fe1 N3 C17 -62.0(6) . . . . ?
N4 Fe1 N3 C17 110.6(6) . . . . ?
N5 Fe1 N3 C17 28.1(6) . . . . ?
O1 Fe1 N3 C10 -103(5) . . . . ?
N1 Fe1 N3 C10 89.0(6) . . . . ?
O4 Fe1 N3 C10 177.9(6) . . . . ?
N4 Fe1 N3 C10 -9.4(6) . . . . ?
N5 Fe1 N3 C10 -91.9(6) . . . . ?
O1 Fe1 N3 C9 136(5) . . . . ?
N1 Fe1 N3 C9 -32.0(6) . . . . ?
O4 Fe1 N3 C9 56.9(6) . . . . ?
N4 Fe1 N3 C9 -130.5(6) . . . . ?
N5 Fe1 N3 C9 147.0(6) . . . . ?
C1 C2 C3 C4 -0.3(14) . . . . ?
O6 S2 O4 Fe1 94(3) . . . . ?
O5 S2 O4 Fe1 -133(3) . . . . ?
C19 S2 O4 Fe1 -22(3) . . . . ?
O1 Fe1 O4 S2 76(3) . . . . ?
N1 Fe1 O4 S2 -29(3) . . . . ?
N4 Fe1 O4 S2 -147(2) . . . . ?
N3 Fe1 O4 S2 -107(3) . . . . ?
N5 Fe1 O4 S2 173(3) . . . . ?
O1 Fe1 N4 C12 -38.7(7) . . . . ?
N1 Fe1 N4 C12 67.8(7) . . . . ?
O4 Fe1 N4 C12 -174.4(12) . . . . ?
N3 Fe1 N4 C12 144.6(7) . . . . ?
N5 Fe1 N4 C12 -134.5(7) . . . . ?
O1 Fe1 N4 C11 -154.3(6) . . . . ?
N1 Fe1 N4 C11 -47.8(6) . . . . ?
O4 Fe1 N4 C11 70.0(15) . . . . ?
N3 Fe1 N4 C11 29.0(6) . . . . ?
N5 Fe1 N4 C11 109.9(6) . . . . ?
O1 Fe1 N4 C13 86.3(7) . . . . ?
N1 Fe1 N4 C13 -167.2(7) . . . . ?
O4 Fe1 N4 C13 -49.4(17) . . . . ?
N3 Fe1 N4 C13 -90.4(7) . . . . ?
N5 Fe1 N4 C13 -9.5(7) . . . . ?
C2 C3 C4 C5 -0.8(16) . . . . ?
C3 C4 C5 C6 0.8(16) . . . . ?
O1 Fe1 N5 C16 173.6(6) . . . . ?
N1 Fe1 N5 C16 -3.2(11) . . . . ?
O4 Fe1 N5 C16 84.5(6) . . . . ?
N4 Fe1 N5 C16 -88.3(6) . . . . ?
N3 Fe1 N5 C16 -5.8(6) . . . . ?
O1 Fe1 N5 C14 -68.8(6) . . . . ?
N1 Fe1 N5 C14 114.4(8) . . . . ?
O4 Fe1 N5 C14 -157.9(6) . . . . ?
N4 Fe1 N5 C14 29.3(6) . . . . ?
N3 Fe1 N5 C14 111.8(6) . . . . ?
O1 Fe1 N5 C15 49.4(7) . . . . ?
N1 Fe1 N5 C15 -127.4(8) . . . . ?
O4 Fe1 N5 C15 -39.7(7) . . . . ?
N4 Fe1 N5 C15 147.6(7) . . . . ?
N3 Fe1 N5 C15 -129.9(7) . . . . ?
C4 C5 C6 C1 0.4(14) . . . . ?
C4 C5 C6 N2 -177.1(9) . . . . ?
N1 C1 C6 C5 -178.4(8) . . . . ?
C2 C1 C6 C5 -1.5(14) . . . . ?
N1 C1 C6 N2 -0.4(10) . . . . ?
C2 C1 C6 N2 176.5(8) . . . . ?
C8 N2 C6 C5 177.9(9) . . . . ?
C7 N2 C6 C5 -1.1(15) . . . . ?
C8 N2 C6 C1 0.0(9) . . . . ?
C7 N2 C6 C1 -179.0(9) . . . . ?
C1 N1 C8 N2 -0.7(10) . . . . ?
Fe1 N1 C8 N2 172.3(5) . . . . ?
C1 N1 C8 C9 179.8(8) . . . . ?
Fe1 N1 C8 C9 -7.2(11) . . . . ?
C6 N2 C8 N1 0.5(10) . . . . ?
C7 N2 C8 N1 179.4(9) . . . . ?
C6 N2 C8 C9 180.0(8) . . . . ?
C7 N2 C8 C9 -1.1(13) . . . . ?
C17 N3 C9 C8 149.0(8) . . . . ?
C10 N3 C9 C8 -83.9(9) . . . . ?
Fe1 N3 C9 C8 35.5(8) . . . . ?
N1 C8 C9 N3 -20.8(12) . . . . ?
N2 C8 C9 N3 159.7(7) . . . . ?
C17 N3 C10 C11 -128.0(9) . . . . ?
C9 N3 C10 C11 104.9(10) . . . . ?
Fe1 N3 C10 C11 -13.1(10) . . . . ?
C12 N4 C11 C10 -167.1(9) . . . . ?
C13 N4 C11 C10 70.4(11) . . . . ?
Fe1 N4 C11 C10 -46.8(10) . . . . ?
N3 C10 C11 N4 42.4(13) . . . . ?
C12 N4 C13 C14 112.2(10) . . . . ?
C11 N4 C13 C14 -127.8(10) . . . . ?
Fe1 N4 C13 C14 -14.1(11) . . . . ?
N4 C13 C14 N5 45.3(13) . . . . ?
C16 N5 C14 C13 67.8(11) . . . . ?
C15 N5 C14 C13 -168.1(9) . . . . ?
Fe1 N5 C14 C13 -49.0(10) . . . . ?
C14 N5 C16 C17 -129.8(9) . . . . ?
C15 N5 C16 C17 106.1(10) . . . . ?
Fe1 N5 C16 C17 -18.6(10) . . . . ?
C10 N3 C17 C16 69.7(11) . . . . ?
C9 N3 C17 C16 -163.5(8) . . . . ?
Fe1 N3 C17 C16 -48.3(9) . . . . ?
N5 C16 C17 N3 46.9(11) . . . . ?
O2 S1 C18 F2 177.6(11) . . . . ?
O3 S1 C18 F2 -60.6(12) . . . . ?
O1 S1 C18 F2 56.7(12) . . . . ?
O2 S1 C18 F1 54.9(12) . . . . ?
O3 S1 C18 F1 176.7(11) . . . . ?
O1 S1 C18 F1 -66.0(11) . . . . ?
O2 S1 C18 F3 -61.3(11) . . . . ?
O3 S1 C18 F3 60.5(11) . . . . ?
O1 S1 C18 F3 177.8(10) . . . . ?
O6 S2 C19 F5 -168.3(14) . . . . ?
O4 S2 C19 F5 -47.6(14) . . . . ?
O5 S2 C19 F5 72.2(14) . . . . ?
O6 S2 C19 F4 58.0(14) . . . . ?
O4 S2 C19 F4 178.7(10) . . . . ?
O5 S2 C19 F4 -61.5(13) . . . . ?
O6 S2 C19 F6 -52.6(12) . . . . ?
O4 S2 C19 F6 68.0(10) . . . . ?
O5 S2 C19 F6 -172.1(10) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.087

_database_code_depnum_ccdc_archive 'CCDC 960139'