# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_wp112-lt
_database_code_depnum_ccdc_archive 'CCDC 1519944'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C3 H8 O'
_chemical_formula_sum            'C36 H28 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         1011.33

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'
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'
F F 0.0727 0.0534 '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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   12.2308(2)
_cell_length_b                   12.6838(2)
_cell_length_c                   13.0436(9)
_cell_angle_alpha                83.137(6)
_cell_angle_beta                 68.061(5)
_cell_angle_gamma                70.096(5)
_cell_volume                     1764.77(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    13423
_cell_measurement_theta_min      6.555
_cell_measurement_theta_max      71.45

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.903
_exptl_crystal_F_000             990
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    18.318
_shelx_estimated_absorpt_T_min   0.029
_shelx_estimated_absorpt_T_max   0.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.302693
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku MM007 rotating anode'
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            24041
_diffrn_reflns_av_unetI/netI     0.0749
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.555
_diffrn_reflns_theta_max         72.075
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             6611
_reflns_number_gt                5074
_reflns_threshold_expression     'I > 2σ(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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX (Dolomanov, 2003) and SXGRAPH in WinGX v2013.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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/[σ²(Fo²)+(0.1309P)²+9.7149P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6611
_refine_ls_number_parameters     478
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0800
_refine_ls_wR_factor_ref         0.2652
_refine_ls_wR_factor_gt          0.2156
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_restrained_S_all      1.213
_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
I1 I 0.49621(7) 1.32391(6) 0.63104(6) 0.0491(3) Uani 1 1 d . . . . .
I2 I 0.83418(8) 1.02076(6) 1.49034(6) 0.0486(3) Uani 1 1 d . . . . .
Fe1 Fe 0.80970(15) 0.86949(11) 0.95676(12) 0.0290(4) Uani 1 1 d . . . . .
S100 S 0.8654(3) 0.4344(2) 0.8111(2) 0.0395(6) Uani 1 1 d . . . . .
F100 F 1.0987(7) 0.3442(7) 0.6935(6) 0.0636(19) Uani 1 1 d . . . . .
O100 O 0.8931(8) 0.5292(6) 0.8319(6) 0.0478(19) Uani 1 1 d . . . . .
F101 F 0.9936(8) 0.4534(6) 0.6023(6) 0.068(2) Uani 1 1 d . . . . .
F102 F 0.9787(8) 0.2906(6) 0.6448(6) 0.068(2) Uani 1 1 d . . . . .
O2 O 0.7019(7) 0.9364(5) 1.0963(5) 0.0340(15) Uani 1 1 d . . . . .
O102 O 0.8786(8) 0.3430(6) 0.8862(6) 0.0467(19) Uani 1 1 d . . . . .
O1 O 0.8205(7) 1.0068(5) 0.8873(6) 0.0351(15) Uani 1 1 d . . . . .
O101 O 0.7529(8) 0.4631(7) 0.7848(7) 0.0482(19) Uani 1 1 d . . . . .
N4 N 0.9274(8) 0.7931(6) 0.8170(6) 0.0323(18) Uani 1 1 d . . . . .
N1 N 0.6628(8) 0.8760(7) 0.9278(6) 0.0322(18) Uani 1 1 d . . . . .
N2 N 0.7975(8) 0.7232(6) 1.0196(6) 0.0327(18) Uani 1 1 d . . . . .
N3 N 0.9609(8) 0.8567(6) 0.9822(6) 0.0308(17) Uani 1 1 d . . . . .
C49 C 1.0526(9) 0.7746(8) 0.8032(8) 0.0301(19) Uani 1 1 d . . . . .
C36 C 0.8608(10) 0.9336(8) 1.1669(8) 0.033(2) Uani 1 1 d . . . . .
C23 C 0.4862(11) 0.6673(9) 1.0133(9) 0.041(2) Uani 1 1 d . . . . .
H23 H 0.4135 0.6565 1.0123 0.049 Uiso 1 1 calc R U . . .
C45 C 1.1529(9) 0.7254(8) 0.7058(8) 0.031(2) Uani 1 1 d . . . . .
C41 C 1.0709(11) 0.8093(7) 0.8918(8) 0.034(2) Uani 1 1 d . . . . .
C43 C 1.2920(10) 0.7455(8) 0.7858(8) 0.036(2) Uani 1 1 d . . . . .
H43 H 1.3748 0.7353 0.7798 0.043 Uiso 1 1 calc R U . . .
C16 C 0.6420(11) 1.0522(8) 0.8305(8) 0.036(2) Uani 1 1 d . . . . .
C14 C 0.5983(9) 1.2202(8) 0.7210(9) 0.035(2) Uani 1 1 d . . . . .
C34 C 0.7927(10) 0.9942(8) 1.3562(8) 0.034(2) Uani 1 1 d . . . . .
C25 C 0.6706(10) 0.6006(8) 1.0643(8) 0.034(2) Uani 1 1 d . . . . .
C37 C 0.9669(9) 0.8899(7) 1.0698(7) 0.0266(18) Uani 1 1 d . . . . .
H37 H 1.0464 0.8848 1.0693 0.032 Uiso 1 1 calc R U . . .
C29 C 0.6970(11) 0.7017(8) 1.0183(8) 0.037(2) Uani 1 1 d . . . . .
C17 C 0.6053(11) 0.9559(8) 0.8780(8) 0.036(2) Uani 1 1 d . . . . .
H17 H 0.5321 0.9511 0.8719 0.043 Uiso 1 1 calc R U . . .
C33 C 0.6673(10) 1.0146(8) 1.3662(8) 0.035(2) Uani 1 1 d . . . . .
H33 H 0.6019 1.0412 1.4345 0.042 Uiso 1 1 calc R U . . .
C21 C 0.6187(10) 0.7819(8) 0.9695(8) 0.034(2) Uani 1 1 d . . . . .
C32 C 0.6399(11) 0.9966(9) 1.2792(9) 0.040(2) Uani 1 1 d . . . . .
H32 H 0.5553 1.0111 1.2884 0.048 Uiso 1 1 calc R U . . .
C27 C 0.8536(10) 0.5477(8) 1.1088(9) 0.037(2) Uani 1 1 d . . . . .
H27 H 0.9107 0.4955 1.1386 0.045 Uiso 1 1 calc R U . . .
C35 C 0.8829(10) 0.9569(8) 1.2590(8) 0.034(2) Uani 1 1 d . . . . .
H35 H 0.9664 0.9456 1.2517 0.041 Uiso 1 1 calc R U . . .
C28 C 0.8731(11) 0.6482(8) 1.0637(8) 0.037(2) Uani 1 1 d . . . . .
H28 H 0.9436 0.6635 1.0646 0.045 Uiso 1 1 calc R U . . .
C22 C 0.5170(11) 0.7647(9) 0.9652(9) 0.041(2) Uani 1 1 d . . . . .
H22 H 0.4664 0.8179 0.9301 0.049 Uiso 1 1 calc R U . . .
C47 C 1.0066(10) 0.7093(9) 0.6345(9) 0.039(2) Uani 1 1 d . . . . .
H47 H 0.9879 0.6859 0.5784 0.046 Uiso 1 1 calc R U . . .
C42 C 1.1920(11) 0.7935(8) 0.8823(9) 0.040(2) Uani 1 1 d . . . . .
H42 H 1.2077 0.8153 0.9413 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5689(10) 1.1286(8) 0.7738(8) 0.033(2) Uani 1 1 d . . . . .
H15 H 0.4973 1.1155 0.7727 0.040 Uiso 1 1 calc R U . . .
C26 C 0.7524(11) 0.5254(8) 1.1096(9) 0.039(2) Uani 1 1 d . . . . .
H26 H 0.7375 0.4579 1.1414 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7706(10) 1.1693(8) 0.7843(8) 0.036(2) Uani 1 1 d . . . . .
H12 H 0.8384 1.1863 0.7891 0.043 Uiso 1 1 calc R U . . .
C11 C 0.7462(10) 1.0720(8) 0.8359(8) 0.031(2) Uani 1 1 d . . . . .
C31 C 0.7339(9) 0.9566(7) 1.1748(8) 0.0279(19) Uani 1 1 d . . . . .
C46 C 1.1209(11) 0.6955(9) 0.6214(9) 0.044(3) Uani 1 1 d . . . . .
H46 H 1.1851 0.6647 0.5538 0.053 Uiso 1 1 calc R U . . .
C48 C 0.9081(10) 0.7604(8) 0.7347(8) 0.034(2) Uani 1 1 d . . . . .
H48 H 0.8247 0.7712 0.7418 0.040 Uiso 1 1 calc R U . . .
C100 C 0.9890(12) 0.3791(9) 0.6812(9) 0.043(3) Uani 1 1 d . . . . .
C44 C 1.2709(10) 0.7138(9) 0.7012(9) 0.040(2) Uani 1 1 d . . . . .
H44 H 1.3398 0.6825 0.6364 0.048 Uiso 1 1 calc R U . . .
C24 C 0.5620(13) 0.5880(10) 1.0617(9) 0.050(3) Uani 1 1 d . . . . .
H24 H 0.5400 0.5235 1.0939 0.060 Uiso 1 1 calc R U . . .
C13 C 0.7019(12) 1.2408(9) 0.7274(9) 0.044(3) Uani 1 1 d . . . . .
H13 H 0.7238 1.3045 0.6922 0.053 Uiso 1 1 calc R U . . .
C200 C 0.6970(7) 0.6652(6) 0.6133(6) 0.076(3) Uani 1 1 d D U . . .
H200 H 0.7893 0.6345 0.5935 0.114 Uiso 1 1 calc R U . . .
O200 O 0.6367(12) 0.6852(9) 0.7335(6) 0.104(4) Uani 1 1 d D U . . .
H20A H 0.6546 0.6244 0.7667 0.156 Uiso 1 1 calc R U . . .
C201 C 0.6514(12) 0.5791(7) 0.5834(8) 0.059(3) Uani 1 1 d D U . . .
H20B H 0.7177 0.5064 0.5681 0.089 Uiso 1 1 calc R U . . .
H20C H 0.6291 0.6039 0.5177 0.089 Uiso 1 1 calc R U . . .
H20D H 0.5782 0.5716 0.6453 0.089 Uiso 1 1 calc R U . . .
C202 C 0.6633(15) 0.7777(7) 0.5563(9) 0.089(4) Uani 1 1 d D U . . .
H20E H 0.5777 0.7979 0.5584 0.134 Uiso 1 1 calc R U . . .
H20F H 0.7203 0.7719 0.4793 0.134 Uiso 1 1 calc R U . . .
H20G H 0.6703 0.8357 0.5947 0.134 Uiso 1 1 calc R U . . .


_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
I1 C14 2.067(10) . ?
I2 C34 2.086(9) . ?
Fe1 O1 1.887(7) . ?
Fe1 O2 1.893(7) . ?
Fe1 N1 1.944(8) . ?
Fe1 N3 1.949(8) . ?
Fe1 N4 1.961(8) . ?
Fe1 N2 1.967(8) . ?
S100 O102 1.431(7) . ?
S100 O100 1.435(7) . ?
S100 O101 1.458(8) . ?
S100 C100 1.816(12) . ?
F100 C100 1.327(14) . ?
F101 C100 1.307(12) . ?
F102 C100 1.331(12) . ?
O2 C31 1.303(11) . ?
O1 C11 1.330(11) . ?
N4 C48 1.321(12) . ?
N4 C49 1.412(12) . ?
N1 C17 1.282(13) . ?
N1 C21 1.440(11) . ?
N2 C28 1.326(13) . ?
N2 C29 1.354(13) . ?
N3 C37 1.299(11) . ?
N3 C41 1.412(13) . ?
C49 C41 1.401(13) . ?
C49 C45 1.418(13) . ?
C36 C35 1.409(13) . ?
C36 C37 1.430(13) . ?
C36 C31 1.444(14) . ?
C23 C24 1.386(17) . ?
C23 C22 1.420(14) . ?
C23 H23 0.9500 . ?
C45 C44 1.377(15) . ?
C45 C46 1.426(15) . ?
C41 C42 1.385(16) . ?
C43 C44 1.355(15) . ?
C43 C42 1.406(15) . ?
C43 H43 0.9500 . ?
C16 C11 1.408(14) . ?
C16 C15 1.421(13) . ?
C16 C17 1.435(13) . ?
C14 C15 1.366(14) . ?
C14 C13 1.410(15) . ?
C34 C35 1.339(14) . ?
C34 C33 1.423(14) . ?
C25 C26 1.384(15) . ?
C25 C24 1.404(16) . ?
C25 C29 1.436(13) . ?
C37 H37 0.9500 . ?
C29 C21 1.413(15) . ?
C17 H17 0.9500 . ?
C33 C32 1.360(14) . ?
C33 H33 0.9500 . ?
C21 C22 1.355(15) . ?
C32 C31 1.426(14) . ?
C32 H32 0.9500 . ?
C27 C26 1.358(15) . ?
C27 C28 1.397(13) . ?
C27 H27 0.9500 . ?
C35 H35 0.9500 . ?
C28 H28 0.9500 . ?
C22 H22 0.9500 . ?
C47 C46 1.294(16) . ?
C47 C48 1.440(14) . ?
C47 H47 0.9500 . ?
C42 H42 0.9500 . ?
C15 H15 0.9500 . ?
C26 H26 0.9500 . ?
C12 C13 1.366(14) . ?
C12 C11 1.403(13) . ?
C12 H12 0.9500 . ?
C46 H46 0.9500 . ?
C48 H48 0.9500 . ?
C44 H44 0.9500 . ?
C24 H24 0.9500 . ?
C13 H13 0.9500 . ?
C200 O200 1.4731(10) . ?
C200 C202 1.5281(10) . ?
C200 C201 1.5282(10) . ?
C200 H200 1.0000 . ?
O200 H20A 0.8400 . ?
C201 H20B 0.9800 . ?
C201 H20C 0.9800 . ?
C201 H20D 0.9800 . ?
C202 H20E 0.9800 . ?
C202 H20F 0.9800 . ?
C202 H20G 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O2 94.3(3) . . ?
O1 Fe1 N1 94.9(3) . . ?
O2 Fe1 N1 87.8(3) . . ?
O1 Fe1 N3 86.5(3) . . ?
O2 Fe1 N3 94.2(3) . . ?
N1 Fe1 N3 177.4(3) . . ?
O1 Fe1 N4 88.3(3) . . ?
O2 Fe1 N4 176.4(3) . . ?
N1 Fe1 N4 94.5(3) . . ?
N3 Fe1 N4 83.4(3) . . ?
O1 Fe1 N2 175.9(3) . . ?
O2 Fe1 N2 88.8(3) . . ?
N1 Fe1 N2 82.5(3) . . ?
N3 Fe1 N2 96.0(3) . . ?
N4 Fe1 N2 88.8(3) . . ?
O102 S100 O100 115.9(5) . . ?
O102 S100 O101 114.1(5) . . ?
O100 S100 O101 114.4(5) . . ?
O102 S100 C100 104.1(5) . . ?
O100 S100 C100 102.9(5) . . ?
O101 S100 C100 103.2(5) . . ?
C31 O2 Fe1 127.0(6) . . ?
C11 O1 Fe1 125.9(6) . . ?
C48 N4 C49 116.4(8) . . ?
C48 N4 Fe1 130.8(8) . . ?
C49 N4 Fe1 112.8(6) . . ?
C17 N1 C21 120.6(9) . . ?
C17 N1 Fe1 125.2(7) . . ?
C21 N1 Fe1 114.2(7) . . ?
C28 N2 C29 118.7(8) . . ?
C28 N2 Fe1 127.7(7) . . ?
C29 N2 Fe1 113.7(7) . . ?
C37 N3 C41 120.2(8) . . ?
C37 N3 Fe1 126.4(7) . . ?
C41 N3 Fe1 113.4(6) . . ?
C41 C49 N4 115.3(9) . . ?
C41 C49 C45 122.3(9) . . ?
N4 C49 C45 122.4(9) . . ?
C35 C36 C37 117.3(9) . . ?
C35 C36 C31 118.8(9) . . ?
C37 C36 C31 123.8(8) . . ?
C24 C23 C22 120.1(10) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C44 C45 C49 117.0(9) . . ?
C44 C45 C46 126.6(10) . . ?
C49 C45 C46 116.4(9) . . ?
C42 C41 C49 117.7(10) . . ?
C42 C41 N3 127.4(9) . . ?
C49 C41 N3 114.9(9) . . ?
C44 C43 C42 120.4(10) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C11 C16 C15 119.8(9) . . ?
C11 C16 C17 123.4(9) . . ?
C15 C16 C17 116.8(9) . . ?
C15 C14 C13 118.2(9) . . ?
C15 C14 I1 120.8(7) . . ?
C13 C14 I1 120.9(8) . . ?
C35 C34 C33 118.3(9) . . ?
C35 C34 I2 121.1(8) . . ?
C33 C34 I2 120.7(7) . . ?
C26 C25 C24 125.6(9) . . ?
C26 C25 C29 117.5(10) . . ?
C24 C25 C29 116.9(10) . . ?
N3 C37 C36 123.8(9) . . ?
N3 C37 H37 118.1 . . ?
C36 C37 H37 118.1 . . ?
N2 C29 C21 117.8(8) . . ?
N2 C29 C25 121.4(10) . . ?
C21 C29 C25 120.8(10) . . ?
N1 C17 C16 125.6(10) . . ?
N1 C17 H17 117.2 . . ?
C16 C17 H17 117.2 . . ?
C32 C33 C34 120.9(10) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C22 C21 C29 120.5(9) . . ?
C22 C21 N1 127.8(10) . . ?
C29 C21 N1 111.7(9) . . ?
C33 C32 C31 122.2(10) . . ?
C33 C32 H32 118.9 . . ?
C31 C32 H32 118.9 . . ?
C26 C27 C28 119.3(10) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C34 C35 C36 123.5(10) . . ?
C34 C35 H35 118.2 . . ?
C36 C35 H35 118.2 . . ?
N2 C28 C27 122.8(10) . . ?
N2 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C21 C22 C23 120.0(10) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C46 C47 C48 119.7(10) . . ?
C46 C47 H47 120.1 . . ?
C48 C47 H47 120.1 . . ?
C41 C42 C43 120.4(10) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C14 C15 C16 122.0(9) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C27 C26 C25 120.2(9) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C13 C12 C11 123.3(10) . . ?
C13 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
O1 C11 C12 118.5(9) . . ?
O1 C11 C16 125.0(8) . . ?
C12 C11 C16 116.5(9) . . ?
O2 C31 C32 119.1(9) . . ?
O2 C31 C36 124.5(9) . . ?
C32 C31 C36 116.2(8) . . ?
C47 C46 C45 121.7(10) . . ?
C47 C46 H46 119.2 . . ?
C45 C46 H46 119.2 . . ?
N4 C48 C47 123.4(10) . . ?
N4 C48 H48 118.3 . . ?
C47 C48 H48 118.3 . . ?
F101 C100 F100 107.6(10) . . ?
F101 C100 F102 107.2(9) . . ?
F100 C100 F102 105.9(10) . . ?
F101 C100 S100 112.8(8) . . ?
F100 C100 S100 110.3(8) . . ?
F102 C100 S100 112.7(8) . . ?
C43 C44 C45 122.3(10) . . ?
C43 C44 H44 118.9 . . ?
C45 C44 H44 118.9 . . ?
C23 C24 C25 121.7(9) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C12 C13 C14 120.1(9) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
O200 C200 C202 107.74(10) . . ?
O200 C200 C201 107.78(10) . . ?
C202 C200 C201 112.99(11) . . ?
O200 C200 H200 109.4 . . ?
C202 C200 H200 109.4 . . ?
C201 C200 H200 109.4 . . ?
C200 O200 H20A 109.5 . . ?
C200 C201 H20B 109.5 . . ?
C200 C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
C200 C201 H20D 109.5 . . ?
H20B C201 H20D 109.5 . . ?
H20C C201 H20D 109.5 . . ?
C200 C202 H20E 109.5 . . ?
C200 C202 H20F 109.5 . . ?
H20E C202 H20F 109.5 . . ?
C200 C202 H20G 109.5 . . ?
H20E C202 H20G 109.5 . . ?
H20F C202 H20G 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Fe1 O2 C31 -89.2(7) . . . . ?
N1 Fe1 O2 C31 176.0(7) . . . . ?
N3 Fe1 O2 C31 -2.5(7) . . . . ?
N2 Fe1 O2 C31 93.5(7) . . . . ?
O2 Fe1 O1 C11 -90.5(8) . . . . ?
N1 Fe1 O1 C11 -2.3(8) . . . . ?
N3 Fe1 O1 C11 175.5(8) . . . . ?
N4 Fe1 O1 C11 92.0(8) . . . . ?
C48 N4 C49 C41 -179.7(8) . . . . ?
Fe1 N4 C49 C41 2.4(10) . . . . ?
C48 N4 C49 C45 0.9(12) . . . . ?
Fe1 N4 C49 C45 -177.0(7) . . . . ?
C41 C49 C45 C44 -0.6(14) . . . . ?
N4 C49 C45 C44 178.7(8) . . . . ?
C41 C49 C45 C46 -179.1(9) . . . . ?
N4 C49 C45 C46 0.2(13) . . . . ?
N4 C49 C41 C42 -179.8(8) . . . . ?
C45 C49 C41 C42 -0.4(13) . . . . ?
N4 C49 C41 N3 0.6(11) . . . . ?
C45 C49 C41 N3 180.0(8) . . . . ?
C37 N3 C41 C42 -0.9(14) . . . . ?
Fe1 N3 C41 C42 177.0(8) . . . . ?
C37 N3 C41 C49 178.8(8) . . . . ?
Fe1 N3 C41 C49 -3.3(9) . . . . ?
C41 N3 C37 C36 -176.9(8) . . . . ?
Fe1 N3 C37 C36 5.5(12) . . . . ?
C35 C36 C37 N3 174.5(8) . . . . ?
C31 C36 C37 N3 -6.5(14) . . . . ?
C28 N2 C29 C21 -179.0(9) . . . . ?
Fe1 N2 C29 C21 2.5(11) . . . . ?
C28 N2 C29 C25 0.6(14) . . . . ?
Fe1 N2 C29 C25 -177.8(7) . . . . ?
C26 C25 C29 N2 -0.4(14) . . . . ?
C24 C25 C29 N2 178.1(9) . . . . ?
C26 C25 C29 C21 179.3(9) . . . . ?
C24 C25 C29 C21 -2.2(14) . . . . ?
C21 N1 C17 C16 -178.3(9) . . . . ?
Fe1 N1 C17 C16 3.0(14) . . . . ?
C11 C16 C17 N1 -1.9(16) . . . . ?
C15 C16 C17 N1 176.9(9) . . . . ?
C35 C34 C33 C32 0.1(14) . . . . ?
I2 C34 C33 C32 -179.5(8) . . . . ?
N2 C29 C21 C22 179.7(9) . . . . ?
C25 C29 C21 C22 0.0(15) . . . . ?
N2 C29 C21 N1 0.3(12) . . . . ?
C25 C29 C21 N1 -179.4(8) . . . . ?
C17 N1 C21 C22 -1.2(15) . . . . ?
Fe1 N1 C21 C22 177.7(9) . . . . ?
C17 N1 C21 C29 178.2(9) . . . . ?
Fe1 N1 C21 C29 -3.0(10) . . . . ?
C34 C33 C32 C31 0.1(15) . . . . ?
C33 C34 C35 C36 -1.9(14) . . . . ?
I2 C34 C35 C36 177.6(7) . . . . ?
C37 C36 C35 C34 -177.5(9) . . . . ?
C31 C36 C35 C34 3.5(14) . . . . ?
C29 N2 C28 C27 0.1(14) . . . . ?
Fe1 N2 C28 C27 178.3(7) . . . . ?
C26 C27 C28 N2 -1.0(15) . . . . ?
C29 C21 C22 C23 2.1(16) . . . . ?
N1 C21 C22 C23 -178.6(10) . . . . ?
C24 C23 C22 C21 -1.9(16) . . . . ?
C49 C41 C42 C43 0.8(13) . . . . ?
N3 C41 C42 C43 -179.6(8) . . . . ?
C44 C43 C42 C41 -0.2(14) . . . . ?
C13 C14 C15 C16 -2.6(15) . . . . ?
I1 C14 C15 C16 176.1(7) . . . . ?
C11 C16 C15 C14 1.9(15) . . . . ?
C17 C16 C15 C14 -176.9(9) . . . . ?
C28 C27 C26 C25 1.2(16) . . . . ?
C24 C25 C26 C27 -178.9(10) . . . . ?
C29 C25 C26 C27 -0.5(15) . . . . ?
Fe1 O1 C11 C12 -177.2(7) . . . . ?
Fe1 O1 C11 C16 3.9(14) . . . . ?
C13 C12 C11 O1 178.6(10) . . . . ?
C13 C12 C11 C16 -2.4(15) . . . . ?
C15 C16 C11 O1 179.5(9) . . . . ?
C17 C16 C11 O1 -1.9(16) . . . . ?
C15 C16 C11 C12 0.6(14) . . . . ?
C17 C16 C11 C12 179.3(9) . . . . ?
Fe1 O2 C31 C32 -173.3(7) . . . . ?
Fe1 O2 C31 C36 2.1(12) . . . . ?
C33 C32 C31 O2 177.1(9) . . . . ?
C33 C32 C31 C36 1.4(14) . . . . ?
C35 C36 C31 O2 -178.5(8) . . . . ?
C37 C36 C31 O2 2.5(14) . . . . ?
C35 C36 C31 C32 -3.0(12) . . . . ?
C37 C36 C31 C32 178.0(8) . . . . ?
C48 C47 C46 C45 2.6(16) . . . . ?
C44 C45 C46 C47 179.6(11) . . . . ?
C49 C45 C46 C47 -2.1(15) . . . . ?
C49 N4 C48 C47 -0.5(13) . . . . ?
Fe1 N4 C48 C47 177.0(7) . . . . ?
C46 C47 C48 N4 -1.3(16) . . . . ?
O102 S100 C100 F101 -178.2(8) . . . . ?
O100 S100 C100 F101 -56.8(9) . . . . ?
O101 S100 C100 F101 62.4(9) . . . . ?
O102 S100 C100 F100 -57.8(8) . . . . ?
O100 S100 C100 F100 63.6(8) . . . . ?
O101 S100 C100 F100 -177.2(7) . . . . ?
O102 S100 C100 F102 60.3(10) . . . . ?
O100 S100 C100 F102 -178.3(8) . . . . ?
O101 S100 C100 F102 -59.1(9) . . . . ?
C42 C43 C44 C45 -0.8(15) . . . . ?
C49 C45 C44 C43 1.2(14) . . . . ?
C46 C45 C44 C43 179.5(10) . . . . ?
C22 C23 C24 C25 -0.4(17) . . . . ?
C26 C25 C24 C23 -179.2(10) . . . . ?
C29 C25 C24 C23 2.4(15) . . . . ?
C11 C12 C13 C14 1.8(16) . . . . ?
C15 C14 C13 C12 0.8(16) . . . . ?
I1 C14 C13 C12 -177.9(8) . . . . ?

_refine_diff_density_max         3.003
_refine_diff_density_min         -3.428
_refine_diff_density_rms         0.238

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_wp133270
_database_code_depnum_ccdc_archive 'CCDC 1519943'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C3 H8 O'
_chemical_formula_sum            'C36 H28 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         1011.33

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   12.4864(12)
_cell_length_b                   12.4925(12)
_cell_length_c                   13.6444(12)
_cell_angle_alpha                65.751(9)
_cell_angle_beta                 82.594(7)
_cell_angle_gamma                69.191(9)
_cell_volume                     1813.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    5086
_cell_measurement_theta_min      1.9542
_cell_measurement_theta_max      29.2538

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             990
_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89487
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      270(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  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16431
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         29.32
_reflns_number_total             8529
_reflns_number_gt                6263
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-seed
_computing_publication_material  'XCIF V6.12 (BrukerAXS, 2001).'

_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)+(0.0617P)²+3.7297P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8529
_refine_ls_number_parameters     479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
I1 I 0.21031(4) 0.50405(4) 0.87024(3) 0.07131(15) Uani 1 1 d . . .
I2 I 0.50593(4) 0.15190(4) 0.00240(3) 0.07237(15) Uani 1 1 d . . .
Fe1 Fe 0.62210(5) 0.19457(5) 0.52135(5) 0.03692(15) Uani 1 1 d . . .
N1 N 0.6341(3) 0.3390(3) 0.5568(3) 0.0383(8) Uani 1 1 d . . .
C7 C 0.5627(4) 0.3901(4) 0.6149(3) 0.0409(9) Uani 1 1 d . . .
H7 H 0.5769 0.4532 0.6249 0.049 Uiso 1 1 calc R . .
C8 C 0.7321(4) 0.3752(4) 0.5134(4) 0.0423(10) Uani 1 1 d . . .
C6 C 0.4639(4) 0.3597(4) 0.6654(3) 0.0391(9) Uani 1 1 d . . .
C4 C 0.3035(5) 0.4035(4) 0.7783(4) 0.0477(11) Uani 1 1 d . . .
C1 C 0.4274(4) 0.2694(4) 0.6547(4) 0.0395(9) Uani 1 1 d . . .
C5 C 0.3983(4) 0.4265(4) 0.7263(4) 0.0470(11) Uani 1 1 d . . .
H5 H 0.4201 0.4880 0.7311 0.056 Uiso 1 1 calc R . .
N3 N 0.6406(3) 0.0308(3) 0.5015(3) 0.0345(7) Uani 1 1 d . . .
C23 C 0.6167(3) 0.0276(4) 0.4133(3) 0.0357(8) Uani 1 1 d . . .
H23 H 0.6254 -0.0501 0.4149 0.043 Uiso 1 1 calc R . .
C24 C 0.6827(3) -0.0819(4) 0.5934(3) 0.0361(8) Uani 1 1 d . . .
C22 C 0.5784(3) 0.1322(4) 0.3135(3) 0.0378(9) Uani 1 1 d . . .
O2 O 0.5577(3) 0.2894(3) 0.3782(3) 0.0478(8) Uani 1 1 d . . .
O1 O 0.4788(3) 0.2096(3) 0.5933(3) 0.0468(7) Uani 1 1 d . . .
N2 N 0.7872(3) 0.2019(3) 0.4638(3) 0.0420(8) Uani 1 1 d . . .
C17 C 0.5524(4) 0.2583(4) 0.2989(4) 0.0425(10) Uani 1 1 d . . .
C10 C 0.8547(5) 0.5007(5) 0.4687(5) 0.0602(14) Uani 1 1 d . . .
H10 H 0.8681 0.5692 0.4689 0.072 Uiso 1 1 calc R . .
C11 C 0.9318(5) 0.4274(5) 0.4239(5) 0.0598(14) Uani 1 1 d . . .
H11 H 0.9976 0.4457 0.3939 0.072 Uiso 1 1 calc R . .
C18 C 0.5174(5) 0.3497(4) 0.1956(4) 0.0557(13) Uani 1 1 d . . .
H18 H 0.5017 0.4327 0.1838 0.067 Uiso 1 1 calc R . .
C15 C 0.8609(4) 0.1280(5) 0.4215(4) 0.0508(11) Uani 1 1 d . . .
H15 H 0.8439 0.0619 0.4203 0.061 Uiso 1 1 calc R . .
C9 C 0.7534(5) 0.4753(4) 0.5156(4) 0.0501(11) Uani 1 1 d . . .
H9 H 0.7019 0.5257 0.5475 0.060 Uiso 1 1 calc R . .
C16 C 0.8112(4) 0.2993(4) 0.4662(4) 0.0418(10) Uani 1 1 d . . .
C12 C 0.9132(4) 0.3233(5) 0.4223(4) 0.0506(11) Uani 1 1 d . . .
C14 C 0.9639(5) 0.1458(5) 0.3782(5) 0.0604(13) Uani 1 1 d . . .
H14 H 1.0145 0.0919 0.3489 0.073 Uiso 1 1 calc R . .
C26 C 0.7342(5) -0.3031(4) 0.6995(4) 0.0532(12) Uani 1 1 d . . .
H26 H 0.7406 -0.3818 0.7048 0.064 Uiso 1 1 calc R . .
C25 C 0.6928(4) -0.1997(4) 0.6031(4) 0.0464(10) Uani 1 1 d . . .
H25 H 0.6722 -0.2104 0.5455 0.056 Uiso 1 1 calc R . .
C32 C 0.7152(4) -0.0675(4) 0.6813(3) 0.0376(9) Uani 1 1 d . . .
C2 C 0.3294(4) 0.2477(4) 0.7105(4) 0.0477(11) Uani 1 1 d . . .
H2 H 0.3056 0.1871 0.7062 0.057 Uiso 1 1 calc R . .
C28 C 0.7569(4) -0.1718(4) 0.7781(4) 0.0492(11) Uani 1 1 d . . .
C3 C 0.2679(4) 0.3125(4) 0.7708(4) 0.0499(11) Uani 1 1 d . . .
H3 H 0.2031 0.2965 0.8064 0.060 Uiso 1 1 calc R . .
C21 C 0.5626(4) 0.1061(4) 0.2266(4) 0.0454(10) Uani 1 1 d . . .
H21 H 0.5763 0.0240 0.2368 0.054 Uiso 1 1 calc R . .
C27 C 0.7646(5) -0.2908(5) 0.7840(4) 0.0563(13) Uani 1 1 d . . .
H27 H 0.7911 -0.3608 0.8471 0.068 Uiso 1 1 calc R . .
C20 C 0.5277(4) 0.1982(4) 0.1276(4) 0.0484(11) Uani 1 1 d . . .
C19 C 0.5053(5) 0.3219(5) 0.1114(4) 0.0564(13) Uani 1 1 d . . .
H19 H 0.4823 0.3851 0.0438 0.068 Uiso 1 1 calc R . .
C13 C 0.9896(5) 0.2414(5) 0.3791(5) 0.0611(14) Uani 1 1 d . . .
H13 H 1.0583 0.2531 0.3508 0.073 Uiso 1 1 calc R . .
N4 N 0.7058(3) 0.0495(3) 0.6696(3) 0.0392(8) Uani 1 1 d . . .
C31 C 0.7390(4) 0.0645(4) 0.7500(4) 0.0478(10) Uani 1 1 d . . .
H31 H 0.7334 0.1442 0.7413 0.057 Uiso 1 1 calc R . .
C30 C 0.7821(5) -0.0347(5) 0.8476(4) 0.0603(13) Uani 1 1 d . . .
H30 H 0.8045 -0.0206 0.9024 0.072 Uiso 1 1 calc R . .
C29 C 0.7913(5) -0.1527(5) 0.8621(4) 0.0617(14) Uani 1 1 d . . .
H29 H 0.8199 -0.2194 0.9267 0.074 Uiso 1 1 calc R . .
S1 S 0.94406(11) -0.14555(12) 1.30856(10) 0.0519(3) Uani 1 1 d . . .
O3 O 0.8457(3) -0.1327(4) 1.3744(3) 0.0705(11) Uani 1 1 d . . .
O4 O 1.0329(4) -0.1137(4) 1.3330(4) 0.0764(12) Uani 1 1 d . . .
O5 O 0.9822(5) -0.2577(4) 1.2889(4) 0.0855(13) Uani 1 1 d . . .
F1 F 0.8463(4) 0.0871(4) 1.1843(4) 0.1046(14) Uani 1 1 d . . .
F2 F 0.9740(4) -0.0164(4) 1.1074(3) 0.1018(14) Uani 1 1 d . . .
F3 F 0.8112(4) -0.0401(5) 1.1381(3) 0.1112(15) Uani 1 1 d . . .
C33 C 0.8915(5) -0.0237(6) 1.1781(5) 0.0671(15) Uani 1 1 d . . .
O6 O 0.7722(5) 0.3598(7) 0.7607(5) 0.128(2) Uani 1 1 d . . .
H6 H 0.8404 0.3483 0.7480 0.153 Uiso 1 1 calc R . .
C36 C 0.9260(6) 0.3482(8) 0.9242(7) 0.097(3) Uani 1 1 d . . .
H36A H 0.9769 0.2635 0.9473 0.146 Uiso 1 1 calc R . .
H36B H 0.9366 0.3851 0.9699 0.146 Uiso 1 1 calc R . .
H36C H 0.9424 0.3943 0.8514 0.146 Uiso 1 1 calc R . .
C34 C 0.7943(10) 0.3508(7) 0.9307(6) 0.114(3) Uani 1 1 d . . .
H34A H 0.7811 0.3016 1.0046 0.136 Uiso 1 1 calc R . .
H34B H 0.7449 0.4360 0.9152 0.136 Uiso 1 1 calc R . .
C35 C 0.7586(9) 0.3095(11) 0.8660(6) 0.117(3) Uani 1 1 d . . .
H35A H 0.7983 0.2205 0.8903 0.141 Uiso 1 1 calc R . .
H35B H 0.6776 0.3215 0.8783 0.141 Uiso 1 1 calc R . .


_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
I1 C4 2.094(4) . ?
I2 C20 2.091(5) . ?
Fe1 O1 1.914(3) . ?
Fe1 O2 1.922(3) . ?
Fe1 N3 2.101(3) . ?
Fe1 N1 2.107(3) . ?
Fe1 N2 2.129(4) . ?
Fe1 N4 2.158(4) . ?
N1 C7 1.289(6) . ?
N1 C8 1.427(6) . ?
C7 C6 1.428(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(6) . ?
C8 C16 1.401(7) . ?
C6 C5 1.402(6) . ?
C6 C1 1.422(5) . ?
C4 C5 1.358(7) . ?
C4 C3 1.403(7) . ?
C1 O1 1.306(5) . ?
C1 C2 1.405(7) . ?
C5 H5 0.9300 . ?
N3 C23 1.296(5) . ?
N3 C24 1.423(5) . ?
C23 C22 1.432(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(6) . ?
C24 C32 1.411(6) . ?
C22 C21 1.405(6) . ?
C22 C17 1.422(6) . ?
O2 C17 1.307(5) . ?
N2 C15 1.315(6) . ?
N2 C16 1.365(5) . ?
C17 C18 1.401(7) . ?
C10 C11 1.349(8) . ?
C10 C9 1.420(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.409(7) . ?
C11 H11 0.9300 . ?
C18 C19 1.369(7) . ?
C18 H18 0.9300 . ?
C15 C14 1.396(7) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
C16 C12 1.413(7) . ?
C12 C13 1.400(8) . ?
C14 C13 1.347(8) . ?
C14 H14 0.9300 . ?
C26 C27 1.340(7) . ?
C26 C25 1.405(7) . ?
C26 H26 0.9300 . ?
C25 H25 0.9300 . ?
C32 N4 1.366(5) . ?
C32 C28 1.412(6) . ?
C2 C3 1.366(7) . ?
C2 H2 0.9300 . ?
C28 C29 1.408(7) . ?
C28 C27 1.424(7) . ?
C3 H3 0.9300 . ?
C21 C20 1.362(7) . ?
C21 H21 0.9300 . ?
C27 H27 0.9300 . ?
C20 C19 1.394(7) . ?
C19 H19 0.9300 . ?
C13 H13 0.9300 . ?
N4 C31 1.324(6) . ?
C31 C30 1.398(7) . ?
C31 H31 0.9300 . ?
C30 C29 1.367(8) . ?
C30 H30 0.9300 . ?
C29 H29 0.9300 . ?
S1 O4 1.421(4) . ?
S1 O3 1.426(4) . ?
S1 O5 1.437(4) . ?
S1 C33 1.812(6) . ?
F1 C33 1.330(7) . ?
F2 C33 1.319(7) . ?
F3 C33 1.313(7) . ?
O6 C35 1.327(9) . ?
O6 H6 0.8200 . ?
C36 C34 1.625(13) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C34 C35 1.373(11) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?

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 O2 96.03(15) . . ?
O1 Fe1 N3 97.16(12) . . ?
O2 Fe1 N3 88.84(13) . . ?
O1 Fe1 N1 88.86(13) . . ?
O2 Fe1 N1 99.68(13) . . ?
N3 Fe1 N1 169.03(13) . . ?
O1 Fe1 N2 165.54(13) . . ?
O2 Fe1 N2 90.97(15) . . ?
N3 Fe1 N2 95.61(13) . . ?
N1 Fe1 N2 77.48(14) . . ?
O1 Fe1 N4 88.77(14) . . ?
O2 Fe1 N4 165.55(13) . . ?
N3 Fe1 N4 77.02(13) . . ?
N1 Fe1 N4 94.02(13) . . ?
N2 Fe1 N4 87.52(14) . . ?
C7 N1 C8 121.2(3) . . ?
C7 N1 Fe1 124.5(3) . . ?
C8 N1 Fe1 114.3(3) . . ?
N1 C7 C6 126.6(4) . . ?
N1 C7 H7 116.7 . . ?
C6 C7 H7 116.7 . . ?
C9 C8 C16 119.6(4) . . ?
C9 C8 N1 125.6(4) . . ?
C16 C8 N1 114.9(3) . . ?
C5 C6 C7 117.2(4) . . ?
C5 C6 C1 118.9(4) . . ?
C7 C6 C1 123.9(4) . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 I1 119.9(3) . . ?
C3 C4 I1 119.9(4) . . ?
O1 C1 C2 119.5(4) . . ?
O1 C1 C6 122.8(4) . . ?
C2 C1 C6 117.7(4) . . ?
C4 C5 C6 121.6(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C23 N3 C24 120.0(3) . . ?
C23 N3 Fe1 124.5(3) . . ?
C24 N3 Fe1 115.5(3) . . ?
N3 C23 C22 126.4(3) . . ?
N3 C23 H23 116.8 . . ?
C22 C23 H23 116.8 . . ?
C25 C24 C32 119.1(4) . . ?
C25 C24 N3 126.2(4) . . ?
C32 C24 N3 114.7(3) . . ?
C21 C22 C17 119.1(4) . . ?
C21 C22 C23 116.6(4) . . ?
C17 C22 C23 124.3(4) . . ?
C17 O2 Fe1 132.7(3) . . ?
C1 O1 Fe1 132.4(3) . . ?
C15 N2 C16 119.5(4) . . ?
C15 N2 Fe1 126.1(3) . . ?
C16 N2 Fe1 114.2(3) . . ?
O2 C17 C18 120.6(4) . . ?
O2 C17 C22 122.1(4) . . ?
C18 C17 C22 117.2(4) . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C19 C18 C17 122.6(4) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
N2 C15 C14 122.1(5) . . ?
N2 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C8 C9 C10 119.5(5) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N2 C16 C8 118.3(4) . . ?
N2 C16 C12 121.1(5) . . ?
C8 C16 C12 120.6(4) . . ?
C13 C12 C11 124.1(5) . . ?
C13 C12 C16 117.3(4) . . ?
C11 C12 C16 118.6(5) . . ?
C13 C14 C15 119.6(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C27 C26 C25 121.4(4) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C24 C25 C26 120.2(5) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
N4 C32 C28 121.4(4) . . ?
N4 C32 C24 118.2(4) . . ?
C28 C32 C24 120.4(4) . . ?
C3 C2 C1 122.2(4) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C29 C28 C32 118.1(4) . . ?
C29 C28 C27 123.7(5) . . ?
C32 C28 C27 118.1(4) . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C20 C21 C22 121.6(4) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C26 C27 C28 120.7(5) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C21 C20 C19 119.9(4) . . ?
C21 C20 I2 119.3(3) . . ?
C19 C20 I2 120.8(4) . . ?
C18 C19 C20 119.5(5) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C14 C13 C12 120.3(5) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C31 N4 C32 119.1(4) . . ?
C31 N4 Fe1 126.8(3) . . ?
C32 N4 Fe1 113.9(3) . . ?
N4 C31 C30 122.5(4) . . ?
N4 C31 H31 118.7 . . ?
C30 C31 H31 118.7 . . ?
C29 C30 C31 119.7(5) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C29 C28 119.1(5) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
O4 S1 O3 115.3(3) . . ?
O4 S1 O5 114.8(3) . . ?
O3 S1 O5 114.5(3) . . ?
O4 S1 C33 102.9(3) . . ?
O3 S1 C33 103.4(3) . . ?
O5 S1 C33 103.6(3) . . ?
F3 C33 F2 107.5(5) . . ?
F3 C33 F1 106.8(6) . . ?
F2 C33 F1 107.0(5) . . ?
F3 C33 S1 112.4(4) . . ?
F2 C33 S1 111.9(4) . . ?
F1 C33 S1 111.0(4) . . ?
C35 O6 H6 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C34 C36 119.1(7) . . ?
C35 C34 H34A 107.5 . . ?
C36 C34 H34A 107.5 . . ?
C35 C34 H34B 107.5 . . ?
C36 C34 H34B 107.5 . . ?
H34A C34 H34B 107.0 . . ?
O6 C35 C34 118.9(8) . . ?
O6 C35 H35A 107.6 . . ?
C34 C35 H35A 107.6 . . ?
O6 C35 H35B 107.6 . . ?
C34 C35 H35B 107.6 . . ?
H35A C35 H35B 107.0 . . ?

_diffrn_measured_fraction_theta_max 0.856
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         2.006
_refine_diff_density_min         -1.470
_refine_diff_density_rms         0.097
####################################################################### 
# 
# 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_100K
_database_code_depnum_ccdc_archive 'CCDC 1519938'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H26 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         997.31

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'
I I -0.4742 1.8119 '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

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

_cell_length_a                   12.430(3)
_cell_length_b                   12.336(3)
_cell_length_c                   13.183(3)
_cell_angle_alpha                111.83(3)
_cell_angle_beta                 99.23(3)
_cell_angle_gamma                66.05(3)
_cell_volume                     1714.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9063
_cell_measurement_theta_min      0.900
_cell_measurement_theta_max      30.070

_exptl_crystal_description       Block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             974
_exptl_absorpt_coefficient_mu    2.371
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'XScale within XDS'

_exptl_special_details           
; 
As the crystal was very tiny after it shattered, the diffractions were thus incredibly weak. 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'Australian Synchrotron, MX2'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'ADSC Quantum 315r CCD'
_diffrn_measurement_method       'Phi Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34873
_diffrn_reflns_av_R_equivalents  0.1036
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         30.07
_reflns_number_total             9063
_reflns_number_gt                6417
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'XCIF V6.12 (BrukerAXS, 2001).'

_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)+(0.0867P)²+1.0578P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9063
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
I2 I 0.11987(4) 0.99887(3) 0.12089(3) 0.03048(11) Uani 1 1 d . . .
I1 I 0.48466(4) 0.69146(4) 1.00079(3) 0.03516(12) Uani 1 1 d . . .
Fe1 Fe 0.61974(7) 0.68979(6) 0.45886(6) 0.01893(16) Uani 1 1 d . . .
S1 S 1.04136(14) 0.63474(13) 0.30074(13) 0.0299(3) Uani 1 1 d . . .
O1 O 0.5542(3) 0.8041(3) 0.5972(3) 0.0225(8) Uani 1 1 d . . .
O2 O 0.4746(3) 0.6841(3) 0.3930(3) 0.0235(8) Uani 1 1 d . . .
F3 F 1.1590(4) 0.3943(4) 0.1961(4) 0.0447(10) Uani 1 1 d . . .
F2 F 1.0231(4) 0.4875(5) 0.1003(4) 0.0505(11) Uani 1 1 d . . .
F1 F 1.1859(4) 0.5196(4) 0.1330(4) 0.0451(10) Uani 1 1 d . . .
O5 O 0.9529(4) 0.6038(4) 0.3273(4) 0.0339(10) Uani 1 1 d . . .
N3 N 0.6051(4) 0.8341(4) 0.4230(4) 0.0206(9) Uani 1 1 d . . .
O3 O 1.1404(4) 0.6282(4) 0.3749(4) 0.0348(10) Uani 1 1 d . . .
N1 N 0.6399(4) 0.5406(4) 0.4910(4) 0.0189(8) Uani 1 1 d . . .
N4 N 0.7736(4) 0.6965(4) 0.5189(4) 0.0205(9) Uani 1 1 d . . .
N2 N 0.6963(4) 0.5646(4) 0.3205(4) 0.0202(8) Uani 1 1 d . . .
O4 O 0.9969(5) 0.7434(5) 0.2653(5) 0.0431(12) Uani 1 1 d . . .
O6 O 0.7471(5) 0.8396(5) 0.2112(5) 0.0455(12) Uani 1 1 d . . .
H6 H 0.8129 0.8186 0.2425 0.055 Uiso 1 1 calc R . .
C23 C 0.5190(5) 0.8905(4) 0.3673(4) 0.0218(10) Uani 1 1 d . . .
H23 H 0.5207 0.9619 0.3569 0.026 Uiso 1 1 calc R . .
C24 C 0.6998(5) 0.8739(5) 0.4614(4) 0.0219(10) Uani 1 1 d . . .
C20 C 0.2418(5) 0.8947(5) 0.2116(5) 0.0239(11) Uani 1 1 d . . .
C17 C 0.4053(5) 0.7520(5) 0.3353(5) 0.0225(10) Uani 1 1 d . . .
C32 C 0.7893(5) 0.7979(5) 0.5128(4) 0.0222(10) Uani 1 1 d . . .
C21 C 0.3379(5) 0.9241(4) 0.2589(4) 0.0229(11) Uani 1 1 d . . .
H21 H 0.3484 0.9924 0.2505 0.027 Uiso 1 1 calc R . .
C15 C 0.7249(5) 0.5832(5) 0.2373(4) 0.0223(10) Uani 1 1 d . . .
H15 H 0.7127 0.6666 0.2437 0.027 Uiso 1 1 calc R . .
C4 C 0.5104(5) 0.7270(5) 0.8653(5) 0.0250(11) Uani 1 1 d . . .
C8 C 0.6864(5) 0.4265(4) 0.4023(4) 0.0201(10) Uani 1 1 d . . .
C16 C 0.7153(5) 0.4431(4) 0.3114(5) 0.0213(10) Uani 1 1 d . . .
C10 C 0.7474(5) 0.2033(5) 0.3012(5) 0.0252(11) Uani 1 1 d . . .
H10 H 0.7572 0.1215 0.2976 0.030 Uiso 1 1 calc R . .
C26 C 0.8127(6) 1.0053(5) 0.4968(5) 0.0288(12) Uani 1 1 d . . .
H26 H 0.8208 1.0759 0.4905 0.035 Uiso 1 1 calc R . .
C9 C 0.7028(5) 0.3064(5) 0.3970(5) 0.0242(11) Uani 1 1 d . . .
H9 H 0.6840 0.2938 0.4578 0.029 Uiso 1 1 calc R . .
C13 C 0.7908(5) 0.3627(5) 0.1291(5) 0.0266(11) Uani 1 1 d . . .
H13 H 0.8214 0.2953 0.0632 0.032 Uiso 1 1 calc R . .
C28 C 0.8908(5) 0.8243(5) 0.5573(5) 0.0252(11) Uani 1 1 d . . .
C31 C 0.8550(5) 0.6208(5) 0.5660(5) 0.0253(11) Uani 1 1 d . . .
H31 H 0.8434 0.5505 0.5690 0.030 Uiso 1 1 calc R . .
C22 C 0.4220(5) 0.8532(4) 0.3205(4) 0.0213(10) Uani 1 1 d . . .
C6 C 0.5683(5) 0.6500(5) 0.6762(4) 0.0210(10) Uani 1 1 d . . .
C27 C 0.9007(5) 0.9308(5) 0.5484(5) 0.0275(11) Uani 1 1 d . . .
H27 H 0.9678 0.9510 0.5779 0.033 Uiso 1 1 calc R . .
C19 C 0.2252(5) 0.7942(5) 0.2232(5) 0.0273(11) Uani 1 1 d . . .
H19 H 0.1595 0.7733 0.1894 0.033 Uiso 1 1 calc R . .
C18 C 0.3047(5) 0.7260(5) 0.2836(5) 0.0262(11) Uani 1 1 d . . .
H18 H 0.2918 0.6586 0.2912 0.031 Uiso 1 1 calc R . .
C30 C 0.9588(5) 0.6410(5) 0.6119(5) 0.0277(12) Uani 1 1 d . . .
H30 H 1.0157 0.5859 0.6462 0.033 Uiso 1 1 calc R . .
C12 C 0.7633(5) 0.3396(5) 0.2166(5) 0.0239(11) Uani 1 1 d . . .
C25 C 0.7118(5) 0.9787(5) 0.4535(5) 0.0246(11) Uani 1 1 d . . .
H25 H 0.6519 1.0315 0.4191 0.029 Uiso 1 1 calc R . .
C3 C 0.4872(6) 0.8491(5) 0.8705(5) 0.0298(12) Uani 1 1 d . . .
H3 H 0.4601 0.9172 0.9368 0.036 Uiso 1 1 calc R . .
C11 C 0.7773(5) 0.2182(5) 0.2125(5) 0.0257(11) Uani 1 1 d . . .
H11 H 0.8073 0.1472 0.1486 0.031 Uiso 1 1 calc R . .
C5 C 0.5503(5) 0.6286(5) 0.7691(5) 0.0242(11) Uani 1 1 d . . .
H5 H 0.5660 0.5451 0.7652 0.029 Uiso 1 1 calc R . .
C7 C 0.6108(5) 0.5403(4) 0.5806(5) 0.0220(10) Uani 1 1 d . . .
H7 H 0.6182 0.4618 0.5836 0.026 Uiso 1 1 calc R . .
C29 C 0.9765(5) 0.7421(5) 0.6062(5) 0.0284(12) Uani 1 1 d . . .
H29 H 1.0467 0.7560 0.6354 0.034 Uiso 1 1 calc R . .
C14 C 0.7727(5) 0.4842(5) 0.1401(5) 0.0260(11) Uani 1 1 d . . .
H14 H 0.7923 0.5011 0.0824 0.031 Uiso 1 1 calc R . .
C2 C 0.5031(5) 0.8728(5) 0.7807(5) 0.0274(11) Uani 1 1 d . . .
H2 H 0.4862 0.9571 0.7863 0.033 Uiso 1 1 calc R . .
C1 C 0.5437(5) 0.7747(5) 0.6810(5) 0.0227(10) Uani 1 1 d . . .
C35 C 1.1053(6) 0.5020(6) 0.1750(6) 0.0362(14) Uani 1 1 d . . .
C33 C 0.7627(9) 0.7940(7) 0.0979(6) 0.0489(19) Uani 1 1 d . . .
H33A H 0.6846 0.8108 0.0613 0.059 Uiso 1 1 calc R . .
H33B H 0.8060 0.7014 0.0736 0.059 Uiso 1 1 calc R . .
C34 C 0.8283(10) 0.8517(8) 0.0627(8) 0.063(3) Uani 1 1 d . . .
H34A H 0.7902 0.9438 0.0923 0.094 Uiso 1 1 calc R . .
H34B H 0.8282 0.8238 -0.0173 0.094 Uiso 1 1 calc R . .
H34C H 0.9096 0.8253 0.0900 0.094 Uiso 1 1 calc R . .


_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
I2 C20 2.088(5) . ?
I1 C4 2.090(5) . ?
Fe1 O2 1.889(4) . ?
Fe1 O1 1.900(4) . ?
Fe1 N3 1.939(4) . ?
Fe1 N1 1.950(4) . ?
Fe1 N4 1.971(5) . ?
Fe1 N2 1.972(5) . ?
S1 O5 1.428(5) . ?
S1 O3 1.439(5) . ?
S1 O4 1.450(5) . ?
S1 C35 1.846(7) . ?
O1 C1 1.323(6) . ?
O2 C17 1.305(6) . ?
F3 C35 1.336(8) . ?
F2 C35 1.320(9) . ?
F1 C35 1.343(8) . ?
N3 C23 1.300(7) . ?
N3 C24 1.406(8) . ?
N1 C7 1.292(7) . ?
N1 C8 1.419(6) . ?
N4 C31 1.321(7) . ?
N4 C32 1.374(7) . ?
N2 C15 1.326(7) . ?
N2 C16 1.380(6) . ?
O6 C33 1.402(9) . ?
O6 H6 0.8400 . ?
C23 C22 1.432(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.400(7) . ?
C24 C32 1.400(7) . ?
C20 C21 1.376(8) . ?
C20 C19 1.400(8) . ?
C17 C18 1.421(8) . ?
C17 C22 1.429(7) . ?
C32 C28 1.413(9) . ?
C21 C22 1.424(7) . ?
C21 H21 0.9500 . ?
C15 C14 1.406(7) . ?
C15 H15 0.9500 . ?
C4 C5 1.376(8) . ?
C4 C3 1.391(8) . ?
C8 C9 1.387(7) . ?
C8 C16 1.410(8) . ?
C16 C12 1.408(7) . ?
C10 C11 1.376(8) . ?
C10 C9 1.406(8) . ?
C10 H10 0.9500 . ?
C26 C27 1.383(9) . ?
C26 C25 1.405(9) . ?
C26 H26 0.9500 . ?
C9 H9 0.9500 . ?
C13 C14 1.376(8) . ?
C13 C12 1.407(8) . ?
C13 H13 0.9500 . ?
C28 C29 1.402(8) . ?
C28 C27 1.415(8) . ?
C31 C30 1.411(9) . ?
C31 H31 0.9500 . ?
C6 C5 1.412(8) . ?
C6 C1 1.421(7) . ?
C6 C7 1.436(7) . ?
C27 H27 0.9500 . ?
C19 C18 1.375(8) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C30 C29 1.380(8) . ?
C30 H30 0.9500 . ?
C12 C11 1.417(7) . ?
C25 H25 0.9500 . ?
C3 C2 1.380(8) . ?
C3 H3 0.9500 . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C7 H7 0.9500 . ?
C29 H29 0.9500 . ?
C14 H14 0.9500 . ?
C2 C1 1.407(8) . ?
C2 H2 0.9500 . ?
C33 C34 1.491(12) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
O2 Fe1 O1 94.88(18) . . ?
O2 Fe1 N3 94.47(18) . . ?
O1 Fe1 N3 87.91(17) . . ?
O2 Fe1 N1 86.50(18) . . ?
O1 Fe1 N1 94.12(17) . . ?
N3 Fe1 N1 177.68(19) . . ?
O2 Fe1 N4 176.30(19) . . ?
O1 Fe1 N4 87.82(18) . . ?
N3 Fe1 N4 83.08(19) . . ?
N1 Fe1 N4 95.85(19) . . ?
O2 Fe1 N2 87.88(19) . . ?
O1 Fe1 N2 176.16(18) . . ?
N3 Fe1 N2 94.56(18) . . ?
N1 Fe1 N2 83.36(18) . . ?
N4 Fe1 N2 89.56(19) . . ?
O5 S1 O3 115.4(3) . . ?
O5 S1 O4 114.9(3) . . ?
O3 S1 O4 114.9(3) . . ?
O5 S1 C35 102.7(3) . . ?
O3 S1 C35 103.2(3) . . ?
O4 S1 C35 103.1(3) . . ?
C1 O1 Fe1 126.8(3) . . ?
C17 O2 Fe1 126.8(3) . . ?
C23 N3 C24 121.0(4) . . ?
C23 N3 Fe1 125.4(4) . . ?
C24 N3 Fe1 113.6(3) . . ?
C7 N1 C8 120.9(4) . . ?
C7 N1 Fe1 125.8(3) . . ?
C8 N1 Fe1 113.3(3) . . ?
C31 N4 C32 119.9(5) . . ?
C31 N4 Fe1 127.8(4) . . ?
C32 N4 Fe1 112.2(4) . . ?
C15 N2 C16 118.6(4) . . ?
C15 N2 Fe1 129.0(3) . . ?
C16 N2 Fe1 112.3(4) . . ?
C33 O6 H6 109.5 . . ?
N3 C23 C22 125.1(5) . . ?
N3 C23 H23 117.5 . . ?
C22 C23 H23 117.5 . . ?
C25 C24 C32 119.0(5) . . ?
C25 C24 N3 127.1(5) . . ?
C32 C24 N3 113.9(5) . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 I2 120.3(4) . . ?
C19 C20 I2 119.4(4) . . ?
O2 C17 C18 118.6(5) . . ?
O2 C17 C22 124.7(5) . . ?
C18 C17 C22 116.7(5) . . ?
N4 C32 C24 116.9(5) . . ?
N4 C32 C28 121.3(5) . . ?
C24 C32 C28 121.8(5) . . ?
C20 C21 C22 120.7(5) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
N2 C15 C14 122.6(5) . . ?
N2 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
C5 C4 C3 119.3(5) . . ?
C5 C4 I1 119.8(4) . . ?
C3 C4 I1 120.9(4) . . ?
C9 C8 C16 119.3(5) . . ?
C9 C8 N1 127.0(5) . . ?
C16 C8 N1 113.7(4) . . ?
N2 C16 C12 121.8(5) . . ?
N2 C16 C8 117.0(5) . . ?
C12 C16 C8 121.2(5) . . ?
C11 C10 C9 121.5(5) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C27 C26 C25 121.3(5) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C14 C13 C12 119.1(5) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C29 C28 C32 117.8(5) . . ?
C29 C28 C27 124.1(6) . . ?
C32 C28 C27 118.1(5) . . ?
N4 C31 C30 122.0(5) . . ?
N4 C31 H31 119.0 . . ?
C30 C31 H31 119.0 . . ?
C21 C22 C17 119.8(5) . . ?
C21 C22 C23 117.1(5) . . ?
C17 C22 C23 123.1(5) . . ?
C5 C6 C1 119.9(5) . . ?
C5 C6 C7 116.2(5) . . ?
C1 C6 C7 123.9(5) . . ?
C26 C27 C28 120.1(6) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C18 C19 C20 119.6(6) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C18 C17 122.8(5) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C29 C30 C31 119.0(5) . . ?
C29 C30 H30 120.5 . . ?
C31 C30 H30 120.5 . . ?
C13 C12 C16 118.3(5) . . ?
C13 C12 C11 123.3(5) . . ?
C16 C12 C11 118.4(5) . . ?
C24 C25 C26 119.7(5) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C10 C11 C12 119.9(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C4 C5 C6 121.0(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N1 C7 C6 124.8(5) . . ?
N1 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C30 C29 C28 120.0(6) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C13 C14 C15 119.7(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C3 C2 C1 121.4(5) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
O1 C1 C2 118.4(4) . . ?
O1 C1 C6 124.1(5) . . ?
C2 C1 C6 117.5(5) . . ?
F2 C35 F3 107.6(6) . . ?
F2 C35 F1 108.8(6) . . ?
F3 C35 F1 107.4(5) . . ?
F2 C35 S1 111.2(5) . . ?
F3 C35 S1 110.6(5) . . ?
F1 C35 S1 111.2(5) . . ?
O6 C33 C34 113.4(7) . . ?
O6 C33 H33A 108.9 . . ?
C34 C33 H33A 108.9 . . ?
O6 C33 H33B 108.9 . . ?
C34 C33 H33B 108.9 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.917
_refine_diff_density_max         1.906
_refine_diff_density_min         -1.566
_refine_diff_density_rms         0.198
####################################################################### 
# 
# 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_wp112_rt
_database_code_depnum_ccdc_archive 'CCDC 1519945'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C3 H8 O'
_chemical_formula_sum            'C36 H28 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         1011.33

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'
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'
F F 0.0727 0.0534 '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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   12.4632(3)
_cell_length_b                   12.6561(3)
_cell_length_c                   13.3650(9)
_cell_angle_alpha                83.298(6)
_cell_angle_beta                 67.300(5)
_cell_angle_gamma                69.644(5)
_cell_volume                     1823.00(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14458
_cell_measurement_theta_min      6.61
_cell_measurement_theta_max      71.355

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_F_000             990
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    17.733
_shelx_estimated_absorpt_T_min   0.030
_shelx_estimated_absorpt_T_max   0.331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.485831
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku MM007 rotating anode'
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            25636
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.612
_diffrn_reflns_theta_max         72.102
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             6809
_reflns_number_gt                4901
_reflns_threshold_expression     'I > 2σ(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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX (Dolomanov, 2003) and SXGRAPH in WinGX v2013.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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/[σ²(Fo²)+(0.1360P)²+2.8104P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6809
_refine_ls_number_parameters     478
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2624
_refine_ls_wR_factor_gt          0.2206
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_restrained_S_all      1.164
_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_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
I1 I 0.49151(7) 1.31314(7) 0.62504(6) 0.0946(3) Uani 1 1 d . . . . .
I2 I 0.84605(8) 1.01230(6) 1.48681(6) 0.0930(3) Uani 1 1 d . . . . .
Fe1 Fe 0.80696(11) 0.87937(9) 0.96081(9) 0.0490(3) Uani 1 1 d . . . . .
S100 S 0.8686(2) 0.43408(17) 0.80968(17) 0.0651(6) Uani 1 1 d . . . . .
F100 F 1.0979(7) 0.3423(8) 0.6883(6) 0.126(3) Uani 1 1 d . . . . .
O100 O 0.8953(9) 0.5273(6) 0.8325(6) 0.101(3) Uani 1 1 d . . . . .
F101 F 0.9911(8) 0.4583(6) 0.6056(5) 0.116(2) Uani 1 1 d . . . . .
F102 F 0.9770(8) 0.2946(6) 0.6427(5) 0.122(3) Uani 1 1 d . . . . .
O2 O 0.7113(5) 0.9461(5) 1.1021(5) 0.0650(14) Uani 1 1 d . . . . .
O102 O 0.8836(7) 0.3421(5) 0.8800(5) 0.0810(19) Uani 1 1 d . . . . .
O1 O 0.8013(6) 1.0192(5) 0.8877(5) 0.0624(14) Uani 1 1 d . . . . .
O101 O 0.7572(7) 0.4626(7) 0.7875(6) 0.097(2) Uani 1 1 d . . . . .
N4 N 0.9423(8) 0.7925(5) 0.8173(6) 0.0638(18) Uani 1 1 d . . . . .
N1 N 0.6593(6) 0.8777(5) 0.9264(5) 0.0497(14) Uani 1 1 d . . . . .
N2 N 0.7934(6) 0.7229(5) 1.0203(5) 0.0513(14) Uani 1 1 d . . . . .
N3 N 0.9666(6) 0.8591(5) 0.9853(5) 0.0473(12) Uani 1 1 d . U . . .
C49 C 1.0641(9) 0.7743(6) 0.8078(7) 0.061(2) Uani 1 1 d . . . . .
C36 C 0.8666(7) 0.9318(5) 1.1712(6) 0.0474(16) Uani 1 1 d . . . . .
C23 C 0.4879(11) 0.6701(10) 1.0117(9) 0.084(3) Uani 1 1 d . . . . .
H23 H 0.4187 0.6596 1.0091 0.100 Uiso 1 1 calc R U . . .
C45 C 1.1660(9) 0.7245(8) 0.7142(7) 0.069(2) Uani 1 1 d . . . . .
C41 C 1.0785(7) 0.8109(6) 0.8963(6) 0.0473(14) Uani 1 1 d . U . . .
C43 C 1.2983(9) 0.7470(8) 0.7945(8) 0.076(2) Uani 1 1 d . U . . .
H43 H 1.3774 0.7369 0.7906 0.091 Uiso 1 1 calc R U . . .
C16 C 0.6385(7) 1.0496(7) 0.8240(7) 0.0554(18) Uani 1 1 d . . . . .
C14 C 0.5958(9) 1.2117(8) 0.7150(7) 0.069(2) Uani 1 1 d . . . . .
C34 C 0.8012(8) 0.9881(7) 1.3574(7) 0.0584(19) Uani 1 1 d . . . . .
C25 C 0.6646(10) 0.6041(7) 1.0636(7) 0.069(2) Uani 1 1 d . . . . .
C37 C 0.9688(8) 0.8875(6) 1.0754(7) 0.0544(18) Uani 1 1 d . . . . .
H37 H 1.0460 0.8774 1.0763 0.065 Uiso 1 1 calc R U . . .
C29 C 0.6939(8) 0.7027(6) 1.0175(6) 0.0548(18) Uani 1 1 d . . . . .
C17 C 0.6041(8) 0.9540(7) 0.8734(6) 0.0570(19) Uani 1 1 d . . . . .
H17 H 0.5358 0.9460 0.8667 0.068 Uiso 1 1 calc R U . . .
C33 C 0.6808(9) 1.0113(7) 1.3697(8) 0.069(2) Uani 1 1 d . . . . .
H33 H 0.6185 1.0369 1.4366 0.083 Uiso 1 1 calc R U . . .
C21 C 0.6186(8) 0.7820(7) 0.9703(7) 0.059(2) Uani 1 1 d . . . . .
C32 C 0.6513(9) 0.9973(8) 1.2850(8) 0.070(2) Uani 1 1 d . . . . .
H32 H 0.5690 1.0138 1.2950 0.084 Uiso 1 1 calc R U . . .
C27 C 0.8433(13) 0.5489(8) 1.1100(9) 0.084(3) Uani 1 1 d . . . . .
H27 H 0.8957 0.4977 1.1407 0.101 Uiso 1 1 calc R U . . .
C35 C 0.8901(8) 0.9495(6) 1.2627(7) 0.0579(19) Uani 1 1 d . . . . .
H35 H 0.9713 0.9332 1.2559 0.070 Uiso 1 1 calc R U . . .
C28 C 0.8658(10) 0.6471(7) 1.0655(7) 0.066(2) Uani 1 1 d . . . . .
H28 H 0.9338 0.6607 1.0671 0.079 Uiso 1 1 calc R U . . .
C22 C 0.5168(9) 0.7650(8) 0.9673(8) 0.070(2) Uani 1 1 d . . . . .
H22 H 0.4672 0.8179 0.9352 0.083 Uiso 1 1 calc R U . . .
C47 C 1.0242(14) 0.7081(9) 0.6403(8) 0.090(3) Uani 1 1 d . . . . .
H47 H 1.0090 0.6856 0.5848 0.108 Uiso 1 1 calc R U . . .
C42 C 1.1948(8) 0.7971(7) 0.8902(7) 0.062(2) Uani 1 1 d . . . . .
H42 H 1.2064 0.8201 0.9477 0.074 Uiso 1 1 calc R U . . .
C15 C 0.5680(8) 1.1215(8) 0.7666(6) 0.0591(19) Uani 1 1 d . . . . .
H15 H 0.5011 1.1062 0.7645 0.071 Uiso 1 1 calc R U . . .
C26 C 0.7434(12) 0.5276(8) 1.1087(8) 0.084(3) Uani 1 1 d . . . . .
H26 H 0.7283 0.4615 1.1381 0.101 Uiso 1 1 calc R U . . .
C12 C 0.7594(9) 1.1726(7) 0.7789(8) 0.067(2) Uani 1 1 d . . . . .
H12 H 0.8234 1.1913 0.7832 0.081 Uiso 1 1 calc R U . . .
C11 C 0.7351(8) 1.0764(6) 0.8324(7) 0.0545(18) Uani 1 1 d . . . . .
C31 C 0.7448(7) 0.9577(6) 1.1811(7) 0.0517(17) Uani 1 1 d . . . . .
C46 C 1.1412(13) 0.6922(10) 0.6305(8) 0.088(3) Uani 1 1 d . . . . .
H46 H 1.2063 0.6594 0.5672 0.106 Uiso 1 1 calc R U . . .
C48 C 0.9250(10) 0.7598(8) 0.7372(7) 0.072(2) Uani 1 1 d . . . . .
H48 H 0.8449 0.7707 0.7436 0.086 Uiso 1 1 calc R U . . .
C100 C 0.9888(12) 0.3807(8) 0.6793(8) 0.081(3) Uani 1 1 d . . . . .
C44 C 1.2832(9) 0.7146(9) 0.7111(9) 0.078(2) Uani 1 1 d . U . . .
H44 H 1.3519 0.6847 0.6491 0.094 Uiso 1 1 calc R U . . .
C24 C 0.5586(12) 0.5915(9) 1.0590(8) 0.085(3) Uani 1 1 d . . . . .
H24 H 0.5368 0.5284 1.0890 0.102 Uiso 1 1 calc R U . . .
C13 C 0.6922(9) 1.2403(8) 0.7202(7) 0.071(2) Uani 1 1 d . . . . .
H13 H 0.7106 1.3033 0.6851 0.085 Uiso 1 1 calc R U . . .
C200 C 0.6957(7) 0.6659(7) 0.6218(7) 0.136(4) Uani 1 1 d D U . . .
H200 H 0.7850 0.6362 0.6037 0.203 Uiso 1 1 calc R U . . .
O200 O 0.6321(13) 0.6796(10) 0.7404(6) 0.196(5) Uani 1 1 d D U . . .
H20A H 0.6520 0.6188 0.7690 0.294 Uiso 1 1 calc R U . . .
C201 C 0.6557(11) 0.5817(7) 0.5838(8) 0.100(3) Uani 1 1 d D U . . .
H20B H 0.7202 0.5099 0.5687 0.150 Uiso 1 1 calc R U . . .
H20C H 0.6392 0.6085 0.5193 0.150 Uiso 1 1 calc R U . . .
H20D H 0.5824 0.5737 0.6397 0.150 Uiso 1 1 calc R U . . .
C202 C 0.6616(15) 0.7821(8) 0.5724(10) 0.148(5) Uani 1 1 d D U . . .
H20E H 0.5793 0.8028 0.5736 0.222 Uiso 1 1 calc R U . . .
H20F H 0.7181 0.7798 0.4988 0.222 Uiso 1 1 calc R U . . .
H20G H 0.6661 0.8366 0.6136 0.222 Uiso 1 1 calc R U . . .


_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
I1 C14 2.113(8) . ?
I2 C34 2.095(8) . ?
Fe1 O1 1.911(6) . ?
Fe1 O2 1.906(6) . ?
Fe1 N2 2.084(6) . ?
Fe1 N4 2.107(8) . ?
Fe1 N1 2.069(6) . ?
Fe1 N3 2.064(6) . ?
S100 O100 1.425(7) . ?
S100 O102 1.415(6) . ?
S100 O101 1.445(8) . ?
S100 C100 1.815(12) . ?
F100 C100 1.324(13) . ?
F101 C100 1.307(11) . ?
F102 C100 1.318(11) . ?
O2 C31 1.315(9) . ?
O1 C11 1.297(9) . ?
N4 C48 1.307(10) . ?
N4 C49 1.410(12) . ?
N1 C17 1.289(10) . ?
N1 C21 1.448(10) . ?
N2 C28 1.335(10) . ?
N2 C29 1.366(10) . ?
N3 C37 1.308(9) . ?
N3 C41 1.424(9) . ?
C49 C45 1.405(12) . ?
C49 C41 1.413(11) . ?
C36 C37 1.410(11) . ?
C36 C35 1.420(11) . ?
C36 C31 1.393(10) . ?
C23 C24 1.357(16) . ?
C23 C22 1.376(14) . ?
C23 H23 0.9300 . ?
C45 C44 1.407(14) . ?
C45 C46 1.405(15) . ?
C41 C42 1.368(11) . ?
C43 C44 1.329(15) . ?
C43 C42 1.432(13) . ?
C43 H43 0.9300 . ?
C16 C11 1.406(11) . ?
C16 C17 1.429(12) . ?
C16 C15 1.409(11) . ?
C14 C15 1.344(13) . ?
C14 C13 1.398(13) . ?
C34 C35 1.323(11) . ?
C34 C33 1.370(12) . ?
C25 C26 1.387(15) . ?
C25 C24 1.408(16) . ?
C25 C29 1.425(11) . ?
C37 H37 0.9300 . ?
C29 C21 1.393(12) . ?
C17 H17 0.9300 . ?
C33 C32 1.365(12) . ?
C33 H33 0.9300 . ?
C21 C22 1.374(12) . ?
C32 C31 1.430(12) . ?
C32 H32 0.9300 . ?
C27 C26 1.368(17) . ?
C27 C28 1.386(12) . ?
C27 H27 0.9300 . ?
C35 H35 0.9300 . ?
C28 H28 0.9300 . ?
C22 H22 0.9300 . ?
C47 C46 1.355(17) . ?
C47 C48 1.426(15) . ?
C47 H47 0.9300 . ?
C42 H42 0.9300 . ?
C15 H15 0.9300 . ?
C26 H26 0.9300 . ?
C12 C13 1.379(12) . ?
C12 C11 1.404(12) . ?
C12 H12 0.9300 . ?
C46 H46 0.9300 . ?
C48 H48 0.9300 . ?
C44 H44 0.9300 . ?
C24 H24 0.9300 . ?
C13 H13 0.9300 . ?
C200 O200 1.4731(10) . ?
C200 C202 1.5279(10) . ?
C200 C201 1.5282(10) . ?
C200 H200 0.9800 . ?
O200 H20A 0.8200 . ?
C201 H20B 0.9600 . ?
C201 H20C 0.9600 . ?
C201 H20D 0.9600 . ?
C202 H20E 0.9600 . ?
C202 H20F 0.9600 . ?
C202 H20G 0.9600 . ?

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 O2 95.2(3) . . ?
O1 Fe1 N2 167.7(2) . . ?
O2 Fe1 N2 90.7(3) . . ?
O1 Fe1 N4 89.7(3) . . ?
O2 Fe1 N4 168.1(3) . . ?
N2 Fe1 N4 86.7(2) . . ?
O1 Fe1 N1 89.7(2) . . ?
O2 Fe1 N1 95.9(2) . . ?
N2 Fe1 N1 79.0(2) . . ?
N4 Fe1 N1 95.0(3) . . ?
O1 Fe1 N3 95.0(2) . . ?
O2 Fe1 N3 90.1(2) . . ?
N2 Fe1 N3 95.8(2) . . ?
N4 Fe1 N3 78.7(3) . . ?
N1 Fe1 N3 172.1(2) . . ?
O100 S100 O102 115.0(5) . . ?
O100 S100 O101 115.4(5) . . ?
O102 S100 O101 113.5(5) . . ?
O100 S100 C100 103.5(5) . . ?
O102 S100 C100 104.5(4) . . ?
O101 S100 C100 102.8(5) . . ?
C31 O2 Fe1 130.8(5) . . ?
C11 O1 Fe1 131.2(5) . . ?
C48 N4 C49 118.5(8) . . ?
C48 N4 Fe1 127.6(7) . . ?
C49 N4 Fe1 113.9(5) . . ?
C17 N1 C21 121.2(6) . . ?
C17 N1 Fe1 125.1(5) . . ?
C21 N1 Fe1 113.7(5) . . ?
C28 N2 C29 118.8(7) . . ?
C28 N2 Fe1 126.9(6) . . ?
C29 N2 Fe1 114.1(5) . . ?
C37 N3 C41 120.5(7) . . ?
C37 N3 Fe1 123.9(6) . . ?
C41 N3 Fe1 115.6(4) . . ?
C45 C49 C41 121.6(9) . . ?
C45 C49 N4 121.9(8) . . ?
C41 C49 N4 116.6(7) . . ?
C37 C36 C35 117.8(7) . . ?
C37 C36 C31 123.6(7) . . ?
C35 C36 C31 118.5(7) . . ?
C24 C23 C22 121.1(10) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C44 C45 C49 117.3(9) . . ?
C44 C45 C46 125.8(10) . . ?
C49 C45 C46 116.9(10) . . ?
C42 C41 N3 126.3(7) . . ?
C42 C41 C49 118.8(8) . . ?
N3 C41 C49 114.9(7) . . ?
C44 C43 C42 121.0(10) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C11 C16 C17 123.6(7) . . ?
C11 C16 C15 119.4(8) . . ?
C17 C16 C15 117.1(7) . . ?
C15 C14 C13 121.1(8) . . ?
C15 C14 I1 119.7(6) . . ?
C13 C14 I1 119.2(7) . . ?
C35 C34 C33 119.6(8) . . ?
C35 C34 I2 119.7(6) . . ?
C33 C34 I2 120.7(6) . . ?
C26 C25 C24 125.1(9) . . ?
C26 C25 C29 117.4(9) . . ?
C24 C25 C29 117.5(10) . . ?
N3 C37 C36 127.0(7) . . ?
N3 C37 H37 116.5 . . ?
C36 C37 H37 116.5 . . ?
N2 C29 C21 118.6(7) . . ?
N2 C29 C25 121.5(8) . . ?
C21 C29 C25 119.9(8) . . ?
N1 C17 C16 125.9(7) . . ?
N1 C17 H17 117.0 . . ?
C16 C17 H17 117.0 . . ?
C32 C33 C34 120.8(8) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C22 C21 C29 120.1(8) . . ?
C22 C21 N1 125.8(8) . . ?
C29 C21 N1 114.1(7) . . ?
C33 C32 C31 121.1(8) . . ?
C33 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C26 C27 C28 119.6(10) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C34 C35 C36 122.8(8) . . ?
C34 C35 H35 118.6 . . ?
C36 C35 H35 118.6 . . ?
N2 C28 C27 122.4(10) . . ?
N2 C28 H28 118.8 . . ?
C27 C28 H28 118.8 . . ?
C21 C22 C23 120.4(10) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C46 C47 C48 119.0(9) . . ?
C46 C47 H47 120.5 . . ?
C48 C47 H47 120.5 . . ?
C41 C42 C43 119.5(9) . . ?
C41 C42 H42 120.3 . . ?
C43 C42 H42 120.3 . . ?
C14 C15 C16 121.2(8) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C27 C26 C25 120.3(9) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C13 C12 C11 122.6(8) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
O1 C11 C12 118.3(7) . . ?
O1 C11 C16 124.2(7) . . ?
C12 C11 C16 117.5(7) . . ?
O2 C31 C32 118.6(7) . . ?
O2 C31 C36 124.2(7) . . ?
C32 C31 C36 117.1(7) . . ?
C47 C46 C45 121.2(10) . . ?
C47 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
N4 C48 C47 122.5(10) . . ?
N4 C48 H48 118.7 . . ?
C47 C48 H48 118.7 . . ?
F101 C100 F102 108.1(8) . . ?
F101 C100 F100 108.3(10) . . ?
F102 C100 F100 105.6(10) . . ?
F101 C100 S100 112.0(8) . . ?
F102 C100 S100 112.4(8) . . ?
F100 C100 S100 110.1(7) . . ?
C43 C44 C45 121.8(10) . . ?
C43 C44 H44 119.1 . . ?
C45 C44 H44 119.1 . . ?
C23 C24 C25 121.0(9) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C12 C13 C14 118.2(8) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
O200 C200 C202 107.74(10) . . ?
O200 C200 C201 107.79(10) . . ?
C202 C200 C201 113.00(11) . . ?
O200 C200 H200 109.4 . . ?
C202 C200 H200 109.4 . . ?
C201 C200 H200 109.4 . . ?
C200 O200 H20A 109.5 . . ?
C200 C201 H20B 109.5 . . ?
C200 C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
C200 C201 H20D 109.5 . . ?
H20B C201 H20D 109.5 . . ?
H20C C201 H20D 109.5 . . ?
C200 C202 H20E 109.5 . . ?
C200 C202 H20F 109.5 . . ?
H20E C202 H20F 109.5 . . ?
C200 C202 H20G 109.5 . . ?
H20E C202 H20G 109.5 . . ?
H20F C202 H20G 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C48 N4 C49 C45 1.4(11) . . . . ?
Fe1 N4 C49 C45 -175.7(6) . . . . ?
C48 N4 C49 C41 180.0(7) . . . . ?
Fe1 N4 C49 C41 3.0(8) . . . . ?
C41 C49 C45 C44 -1.3(12) . . . . ?
N4 C49 C45 C44 177.2(8) . . . . ?
C41 C49 C45 C46 -179.3(8) . . . . ?
N4 C49 C45 C46 -0.7(12) . . . . ?
C37 N3 C41 C42 -5.2(10) . . . . ?
Fe1 N3 C41 C42 174.8(6) . . . . ?
C37 N3 C41 C49 174.3(6) . . . . ?
Fe1 N3 C41 C49 -5.7(7) . . . . ?
C45 C49 C41 C42 -0.1(11) . . . . ?
N4 C49 C41 C42 -178.7(7) . . . . ?
C45 C49 C41 N3 -179.7(7) . . . . ?
N4 C49 C41 N3 1.7(9) . . . . ?
C41 N3 C37 C36 -177.4(6) . . . . ?
Fe1 N3 C37 C36 2.6(10) . . . . ?
C35 C36 C37 N3 175.6(7) . . . . ?
C31 C36 C37 N3 -3.7(12) . . . . ?
C28 N2 C29 C21 180.0(7) . . . . ?
Fe1 N2 C29 C21 4.2(9) . . . . ?
C28 N2 C29 C25 1.3(11) . . . . ?
Fe1 N2 C29 C25 -174.5(6) . . . . ?
C26 C25 C29 N2 -1.9(12) . . . . ?
C24 C25 C29 N2 178.7(7) . . . . ?
C26 C25 C29 C21 179.4(8) . . . . ?
C24 C25 C29 C21 0.0(12) . . . . ?
C21 N1 C17 C16 -178.0(7) . . . . ?
Fe1 N1 C17 C16 3.6(11) . . . . ?
C11 C16 C17 N1 -3.7(13) . . . . ?
C15 C16 C17 N1 178.1(8) . . . . ?
C35 C34 C33 C32 -1.3(14) . . . . ?
I2 C34 C33 C32 178.9(7) . . . . ?
N2 C29 C21 C22 -179.2(7) . . . . ?
C25 C29 C21 C22 -0.5(12) . . . . ?
N2 C29 C21 N1 1.4(10) . . . . ?
C25 C29 C21 N1 -179.8(7) . . . . ?
C17 N1 C21 C22 -4.3(12) . . . . ?
Fe1 N1 C21 C22 174.3(7) . . . . ?
C17 N1 C21 C29 175.0(7) . . . . ?
Fe1 N1 C21 C29 -6.4(8) . . . . ?
C34 C33 C32 C31 0.2(14) . . . . ?
C33 C34 C35 C36 0.8(13) . . . . ?
I2 C34 C35 C36 -179.5(6) . . . . ?
C37 C36 C35 C34 -178.4(7) . . . . ?
C31 C36 C35 C34 0.9(11) . . . . ?
C29 N2 C28 C27 -0.2(12) . . . . ?
Fe1 N2 C28 C27 175.0(7) . . . . ?
C26 C27 C28 N2 -0.2(15) . . . . ?
C29 C21 C22 C23 0.5(13) . . . . ?
N1 C21 C22 C23 179.8(8) . . . . ?
C24 C23 C22 C21 0.0(15) . . . . ?
N3 C41 C42 C43 180.0(7) . . . . ?
C49 C41 C42 C43 0.5(11) . . . . ?
C44 C43 C42 C41 0.7(13) . . . . ?
C13 C14 C15 C16 -2.8(14) . . . . ?
I1 C14 C15 C16 177.6(6) . . . . ?
C11 C16 C15 C14 3.7(12) . . . . ?
C17 C16 C15 C14 -178.1(8) . . . . ?
C28 C27 C26 C25 -0.4(16) . . . . ?
C24 C25 C26 C27 -179.2(10) . . . . ?
C29 C25 C26 C27 1.4(14) . . . . ?
Fe1 O1 C11 C12 -174.1(6) . . . . ?
Fe1 O1 C11 C16 7.1(12) . . . . ?
C13 C12 C11 O1 -178.4(9) . . . . ?
C13 C12 C11 C16 0.4(13) . . . . ?
C17 C16 C11 O1 -1.7(13) . . . . ?
C15 C16 C11 O1 176.4(8) . . . . ?
C17 C16 C11 C12 179.5(8) . . . . ?
C15 C16 C11 C12 -2.4(12) . . . . ?
Fe1 O2 C31 C32 -171.2(6) . . . . ?
Fe1 O2 C31 C36 7.5(11) . . . . ?
C33 C32 C31 O2 -179.7(8) . . . . ?
C33 C32 C31 C36 1.5(12) . . . . ?
C37 C36 C31 O2 -1.4(11) . . . . ?
C35 C36 C31 O2 179.3(7) . . . . ?
C37 C36 C31 C32 177.3(7) . . . . ?
C35 C36 C31 C32 -2.0(10) . . . . ?
C48 C47 C46 C45 0.8(16) . . . . ?
C44 C45 C46 C47 -178.2(10) . . . . ?
C49 C45 C46 C47 -0.4(15) . . . . ?
C49 N4 C48 C47 -0.9(12) . . . . ?
Fe1 N4 C48 C47 175.7(7) . . . . ?
C46 C47 C48 N4 -0.1(15) . . . . ?
O100 S100 C100 F101 -56.2(9) . . . . ?
O102 S100 C100 F101 -176.9(8) . . . . ?
O101 S100 C100 F101 64.3(9) . . . . ?
O100 S100 C100 F102 -178.1(8) . . . . ?
O102 S100 C100 F102 61.2(9) . . . . ?
O101 S100 C100 F102 -57.6(9) . . . . ?
O100 S100 C100 F100 64.4(8) . . . . ?
O102 S100 C100 F100 -56.3(8) . . . . ?
O101 S100 C100 F100 -175.1(8) . . . . ?
C42 C43 C44 C45 -2.2(15) . . . . ?
C49 C45 C44 C43 2.5(14) . . . . ?
C46 C45 C44 C43 -179.7(10) . . . . ?
C22 C23 C24 C25 -0.5(15) . . . . ?
C26 C25 C24 C23 -178.9(10) . . . . ?
C29 C25 C24 C23 0.5(14) . . . . ?
C11 C12 C13 C14 0.4(14) . . . . ?
C15 C14 C13 C12 0.8(14) . . . . ?
I1 C14 C13 C12 -179.7(7) . . . . ?

_refine_diff_density_max         1.755
_refine_diff_density_min         -1.816
_refine_diff_density_rms         0.155

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_wp110lt
_database_code_depnum_ccdc_archive 'CCDC 1519948'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C2 H3 N'
_chemical_formula_sum            'C35 H23 F3 Fe I2 N5 O5 S'
_chemical_formula_weight         992.29

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'
I I -0.4742 1.8119 '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

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

_cell_length_a                   12.0127(13)
_cell_length_b                   12.6193(13)
_cell_length_c                   13.2123(14)
_cell_angle_alpha                110.546(4)
_cell_angle_beta                 92.310(4)
_cell_angle_gamma                111.271(2)
_cell_volume                     1715.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    4776
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            dark
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             966
_exptl_absorpt_coefficient_mu    2.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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  'APEX X8'
_diffrn_measurement_method       'scans in phi and omega'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11294
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         27.49
_reflns_number_total             7642
_reflns_number_gt                6285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2 V2.0'
_computing_cell_refinement       'Bruker Apex2 V2.0'
_computing_data_reduction        'Bruker Apex2 V2.0'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'XCIF V6.12 (BrukerAXS, 2001).'

_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)+(0.0360P)²+28.7382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7642
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1470
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
I1 I 0.08152(4) 0.71993(5) -0.38792(4) 0.01709(13) Uani 1 1 d . . .
I2 I 1.00631(4) 0.64700(5) -0.04060(4) 0.01771(13) Uani 1 1 d . . .
Fe1 Fe 0.46264(9) 0.78680(9) 0.12009(8) 0.0096(2) Uani 1 1 d . . .
S1 S 0.82423(16) 0.75095(17) 0.40961(14) 0.0148(3) Uani 1 1 d . . .
C9 C 0.4580(7) 1.1378(7) 0.2197(7) 0.0194(15) Uani 1 1 d . . .
H9 H 0.4129 1.1441 0.1630 0.023 Uiso 1 1 calc R . .
O3 O 0.9230(5) 0.7130(5) 0.4151(5) 0.0237(12) Uani 1 1 d . . .
O2 O 0.6031(4) 0.8468(5) 0.0635(4) 0.0131(10) Uani 1 1 d . . .
F1 F 0.6928(6) 0.5569(5) 0.4490(5) 0.0461(16) Uani 1 1 d . . .
O1 O 0.3707(4) 0.6682(5) -0.0174(4) 0.0130(10) Uani 1 1 d . . .
N3 N 0.5005(5) 0.6579(5) 0.1402(5) 0.0113(11) Uani 1 1 d . . .
N4 N 0.3244(5) 0.7271(5) 0.1896(5) 0.0117(11) Uani 1 1 d . . .
N1 N 0.4242(5) 0.9181(5) 0.1058(5) 0.0098(11) Uani 1 1 d . . .
F3 F 0.7723(5) 0.7264(5) 0.5928(4) 0.0361(13) Uani 1 1 d . . .
O4 O 0.7500(5) 0.6970(5) 0.3008(4) 0.0240(12) Uani 1 1 d . . .
C17 C 0.6819(6) 0.7967(6) 0.0390(6) 0.0121(13) Uani 1 1 d . . .
C5 C 0.2491(6) 0.8129(7) -0.1684(6) 0.0129(13) Uani 1 1 d . . .
H5 H 0.2498 0.8908 -0.1608 0.016 Uiso 1 1 calc R . .
N2 N 0.5467(5) 0.9107(6) 0.2688(5) 0.0130(12) Uani 1 1 d . . .
C25 C 0.4265(7) 0.5021(7) 0.2259(6) 0.0180(15) Uani 1 1 d . . .
H25 H 0.4915 0.4764 0.2118 0.022 Uiso 1 1 calc R . .
C1 C 0.3140(6) 0.6877(7) -0.0922(6) 0.0131(13) Uani 1 1 d . . .
C16 C 0.5346(6) 1.0219(6) 0.2909(6) 0.0115(13) Uani 1 1 d . . .
C7 C 0.3697(6) 0.9127(6) 0.0168(6) 0.0125(13) Uani 1 1 d . . .
H7 H 0.3664 0.9868 0.0168 0.015 Uiso 1 1 calc R . .
C22 C 0.6785(6) 0.6902(7) 0.0552(6) 0.0125(13) Uani 1 1 d . . .
O5 O 0.8516(6) 0.8783(5) 0.4686(5) 0.0263(13) Uani 1 1 d . . .
C24 C 0.4193(6) 0.5938(6) 0.1948(5) 0.0119(13) Uani 1 1 d . . .
C28 C 0.2359(6) 0.5798(7) 0.2745(6) 0.0139(14) Uani 1 1 d . . .
C20 C 0.8660(6) 0.7081(7) -0.0102(6) 0.0142(14) Uani 1 1 d . . .
C32 C 0.3242(6) 0.6326(6) 0.2202(5) 0.0126(13) Uani 1 1 d . . .
C21 C 0.7710(7) 0.6477(6) 0.0299(6) 0.0142(14) Uani 1 1 d . . .
H21 H 0.7675 0.5761 0.0408 0.017 Uiso 1 1 calc R . .
C8 C 0.4708(6) 1.0286(7) 0.2032(6) 0.0142(14) Uani 1 1 d . . .
C2 C 0.2498(6) 0.5844(7) -0.1931(6) 0.0146(14) Uani 1 1 d . . .
H2 H 0.2507 0.5062 -0.2041 0.017 Uiso 1 1 calc R . .
C12 C 0.5853(6) 1.1216(7) 0.3941(6) 0.0142(14) Uani 1 1 d . . .
C27 C 0.2440(7) 0.4846(7) 0.3029(6) 0.0187(15) Uani 1 1 d . . .
H27 H 0.1850 0.4462 0.3389 0.022 Uiso 1 1 calc R . .
C18 C 0.7814(7) 0.8547(7) -0.0054(6) 0.0160(14) Uani 1 1 d . . .
H18 H 0.7861 0.9255 -0.0184 0.019 Uiso 1 1 calc R . .
C14 C 0.6590(7) 0.9947(7) 0.4526(6) 0.0200(16) Uani 1 1 d . . .
H14 H 0.7016 0.9831 0.5072 0.024 Uiso 1 1 calc R . .
C6 C 0.3137(6) 0.8034(7) -0.0819(6) 0.0125(13) Uani 1 1 d . . .
C35 C 0.7229(8) 0.6771(8) 0.4859(7) 0.0243(17) Uani 1 1 d . . .
C13 C 0.6455(7) 1.1036(7) 0.4761(6) 0.0213(16) Uani 1 1 d . . .
H13 H 0.6770 1.1671 0.5479 0.026 Uiso 1 1 calc R . .
C3 C 0.1870(7) 0.5965(7) -0.2744(6) 0.0157(14) Uani 1 1 d . . .
H3 H 0.1434 0.5259 -0.3400 0.019 Uiso 1 1 calc R . .
C23 C 0.5874(6) 0.6267(6) 0.1043(6) 0.0117(13) Uani 1 1 d . . .
H23 H 0.5909 0.5555 0.1112 0.014 Uiso 1 1 calc R . .
C29 C 0.1419(6) 0.6240(7) 0.2956(6) 0.0151(14) Uani 1 1 d . . .
H29 H 0.0798 0.5897 0.3312 0.018 Uiso 1 1 calc R . .
F2 F 0.6187(5) 0.6944(6) 0.4791(5) 0.0484(16) Uani 1 1 d . . .
C10 C 0.5127(7) 1.2399(7) 0.3217(7) 0.0215(16) Uani 1 1 d . . .
H10 H 0.5079 1.3161 0.3309 0.026 Uiso 1 1 calc R . .
C15 C 0.6093(6) 0.9009(7) 0.3475(6) 0.0160(14) Uani 1 1 d . . .
H15 H 0.6210 0.8267 0.3317 0.019 Uiso 1 1 calc R . .
C19 C 0.8700(7) 0.8116(7) -0.0297(7) 0.0181(15) Uani 1 1 d . . .
H19 H 0.9347 0.8518 -0.0599 0.022 Uiso 1 1 calc R . .
C4 C 0.1859(7) 0.7107(7) -0.2627(6) 0.0152(14) Uani 1 1 d . . .
C26 C 0.3375(7) 0.4477(8) 0.2784(7) 0.0222(17) Uani 1 1 d . . .
H26 H 0.3418 0.3832 0.2976 0.027 Uiso 1 1 calc R . .
C11 C 0.5718(7) 1.2319(7) 0.4064(6) 0.0198(16) Uani 1 1 d . . .
H11 H 0.6045 1.3012 0.4748 0.024 Uiso 1 1 calc R . .
C30 C 0.1423(6) 0.7163(7) 0.2638(6) 0.0156(14) Uani 1 1 d . . .
H30 H 0.0803 0.7466 0.2773 0.019 Uiso 1 1 calc R . .
C31 C 0.2356(6) 0.7667(7) 0.2108(6) 0.0142(14) Uani 1 1 d . . .
H31 H 0.2348 0.8310 0.1895 0.017 Uiso 1 1 calc R . .
N5 N 1.1595(7) 0.9871(7) 0.1716(7) 0.0305(17) Uani 1 1 d . . .
C33 C 1.0809(8) 0.9770(8) 0.2166(7) 0.0274(18) Uani 1 1 d . . .
C34 C 0.9768(9) 0.9636(9) 0.2739(8) 0.032(2) Uani 1 1 d . . .
H34A H 0.9352 1.0133 0.2618 0.048 Uiso 1 1 calc R . .
H34B H 1.0062 0.9920 0.3530 0.048 Uiso 1 1 calc R . .
H34C H 0.9198 0.8765 0.2449 0.048 Uiso 1 1 calc R . .


_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
I1 C4 2.096(7) . ?
I2 C20 2.092(7) . ?
Fe1 O1 1.868(5) . ?
Fe1 O2 1.884(5) . ?
Fe1 N3 1.937(6) . ?
Fe1 N1 1.940(6) . ?
Fe1 N2 1.965(6) . ?
Fe1 N4 1.967(6) . ?
S1 O5 1.420(6) . ?
S1 O3 1.440(6) . ?
S1 O4 1.448(6) . ?
S1 C35 1.817(8) . ?
C9 C8 1.384(10) . ?
C9 C10 1.416(11) . ?
C9 H9 0.9500 . ?
O2 C17 1.310(8) . ?
F1 C35 1.318(10) . ?
O1 C1 1.318(8) . ?
N3 C23 1.295(9) . ?
N3 C24 1.422(9) . ?
N4 C31 1.335(9) . ?
N4 C32 1.385(9) . ?
N1 C7 1.290(9) . ?
N1 C8 1.424(9) . ?
F3 C35 1.335(10) . ?
C17 C22 1.421(10) . ?
C17 C18 1.426(10) . ?
C5 C4 1.370(10) . ?
C5 C6 1.419(9) . ?
C5 H5 0.9500 . ?
N2 C15 1.326(9) . ?
N2 C16 1.392(9) . ?
C25 C24 1.385(10) . ?
C25 C26 1.399(10) . ?
C25 H25 0.9500 . ?
C1 C6 1.420(10) . ?
C1 C2 1.428(10) . ?
C16 C12 1.410(10) . ?
C16 C8 1.407(10) . ?
C7 C6 1.432(10) . ?
C7 H7 0.9500 . ?
C22 C21 1.403(10) . ?
C22 C23 1.431(9) . ?
C24 C32 1.407(10) . ?
C28 C32 1.403(10) . ?
C28 C27 1.412(10) . ?
C28 C29 1.427(10) . ?
C20 C21 1.367(10) . ?
C20 C19 1.401(10) . ?
C21 H21 0.9500 . ?
C2 C3 1.371(10) . ?
C2 H2 0.9500 . ?
C12 C13 1.406(10) . ?
C12 C11 1.413(10) . ?
C27 C26 1.373(11) . ?
C27 H27 0.9500 . ?
C18 C19 1.363(10) . ?
C18 H18 0.9500 . ?
C14 C13 1.370(11) . ?
C14 C15 1.397(11) . ?
C14 H14 0.9500 . ?
C35 F2 1.351(10) . ?
C13 H13 0.9500 . ?
C3 C4 1.400(10) . ?
C3 H3 0.9500 . ?
C23 H23 0.9500 . ?
C29 C30 1.369(10) . ?
C29 H29 0.9500 . ?
C10 C11 1.353(11) . ?
C10 H10 0.9500 . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?
C26 H26 0.9500 . ?
C11 H11 0.9500 . ?
C30 C31 1.418(10) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
N5 C33 1.128(11) . ?
C33 C34 1.476(13) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O2 93.9(2) . . ?
O1 Fe1 N3 86.9(2) . . ?
O2 Fe1 N3 94.6(2) . . ?
O1 Fe1 N1 94.7(2) . . ?
O2 Fe1 N1 86.6(2) . . ?
N3 Fe1 N1 177.8(2) . . ?
O1 Fe1 N2 175.3(2) . . ?
O2 Fe1 N2 90.5(2) . . ?
N3 Fe1 N2 94.5(2) . . ?
N1 Fe1 N2 83.8(2) . . ?
O1 Fe1 N4 89.8(2) . . ?
O2 Fe1 N4 175.6(2) . . ?
N3 Fe1 N4 83.1(2) . . ?
N1 Fe1 N4 95.5(2) . . ?
N2 Fe1 N4 85.9(2) . . ?
O5 S1 O3 116.3(4) . . ?
O5 S1 O4 114.8(3) . . ?
O3 S1 O4 114.1(3) . . ?
O5 S1 C35 103.0(4) . . ?
O3 S1 C35 103.0(4) . . ?
O4 S1 C35 103.1(4) . . ?
C8 C9 C10 119.4(7) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C17 O2 Fe1 126.2(4) . . ?
C1 O1 Fe1 126.1(4) . . ?
C23 N3 C24 121.4(6) . . ?
C23 N3 Fe1 124.9(5) . . ?
C24 N3 Fe1 113.7(4) . . ?
C31 N4 C32 118.4(6) . . ?
C31 N4 Fe1 128.4(5) . . ?
C32 N4 Fe1 113.2(5) . . ?
C7 N1 C8 121.6(6) . . ?
C7 N1 Fe1 125.3(5) . . ?
C8 N1 Fe1 112.9(4) . . ?
O2 C17 C22 125.6(6) . . ?
O2 C17 C18 117.9(6) . . ?
C22 C17 C18 116.6(6) . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C15 N2 C16 118.1(6) . . ?
C15 N2 Fe1 129.0(5) . . ?
C16 N2 Fe1 112.8(4) . . ?
C24 C25 C26 119.6(7) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
O1 C1 C6 125.5(6) . . ?
O1 C1 C2 117.4(6) . . ?
C6 C1 C2 117.2(6) . . ?
N2 C16 C12 121.8(6) . . ?
N2 C16 C8 115.7(6) . . ?
C12 C16 C8 122.5(6) . . ?
N1 C7 C6 124.9(6) . . ?
N1 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C21 C22 C17 120.5(6) . . ?
C21 C22 C23 117.0(6) . . ?
C17 C22 C23 122.4(6) . . ?
C25 C24 C32 118.8(6) . . ?
C25 C24 N3 127.1(6) . . ?
C32 C24 N3 114.0(6) . . ?
C32 C28 C27 118.1(7) . . ?
C32 C28 C29 117.9(6) . . ?
C27 C28 C29 124.0(7) . . ?
C21 C20 C19 120.0(6) . . ?
C21 C20 I2 119.8(5) . . ?
C19 C20 I2 120.2(5) . . ?
N4 C32 C28 122.3(6) . . ?
N4 C32 C24 115.9(6) . . ?
C28 C32 C24 121.8(6) . . ?
C20 C21 C22 120.8(7) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C9 C8 C16 118.3(7) . . ?
C9 C8 N1 127.0(7) . . ?
C16 C8 N1 114.7(6) . . ?
C3 C2 C1 120.9(7) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C16 C12 C13 117.5(7) . . ?
C16 C12 C11 117.1(7) . . ?
C13 C12 C11 125.4(7) . . ?
C26 C27 C28 119.8(7) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
C19 C18 C17 121.9(7) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C13 C14 C15 119.3(7) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C5 C6 C1 120.3(7) . . ?
C5 C6 C7 116.8(6) . . ?
C1 C6 C7 122.7(6) . . ?
F1 C35 F3 108.1(7) . . ?
F1 C35 F2 107.4(7) . . ?
F3 C35 F2 106.6(7) . . ?
F1 C35 S1 113.0(6) . . ?
F3 C35 S1 111.4(6) . . ?
F2 C35 S1 110.1(6) . . ?
C14 C13 C12 120.1(7) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C2 C3 C4 121.4(7) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
N3 C23 C22 125.7(6) . . ?
N3 C23 H23 117.2 . . ?
C22 C23 H23 117.2 . . ?
C30 C29 C28 119.2(7) . . ?
C30 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C11 C10 C9 121.9(7) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N2 C15 C14 123.1(7) . . ?
N2 C15 H15 118.4 . . ?
C14 C15 H15 118.4 . . ?
C18 C19 C20 120.3(7) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C5 C4 C3 119.5(6) . . ?
C5 C4 I1 121.5(5) . . ?
C3 C4 I1 119.0(5) . . ?
C27 C26 C25 121.9(7) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C10 C11 C12 120.6(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C29 C30 C31 119.8(7) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
N4 C31 C30 122.4(7) . . ?
N4 C31 H31 118.8 . . ?
C30 C31 H31 118.8 . . ?
N5 C33 C34 179.1(10) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         3.172
_refine_diff_density_min         -1.791
_refine_diff_density_rms         0.199
####################################################################### 
# 
# 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_wp111ip
_database_code_depnum_ccdc_archive 'CCDC 1519939'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C2 H6 O'
_chemical_formula_sum            'C35 H26 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         997.31

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 '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'
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'

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

_cell_length_a                   11.4760(12)
_cell_length_b                   13.0698(16)
_cell_length_c                   13.4649(16)
_cell_angle_alpha                71.342(11)
_cell_angle_beta                 87.437(9)
_cell_angle_gamma                68.674(11)
_cell_volume                     1776.5(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    170.00(10)
_cell_measurement_reflns_used    4311
_cell_measurement_theta_min      1.9074
_cell_measurement_theta_max      29.0112

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.864
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             974
_exptl_absorpt_coefficient_mu    2.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5985
_exptl_absorpt_correction_T_max  0.7708
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170.00(10)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3389
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14824
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         29.08
_reflns_number_total             8087
_reflns_number_gt                5954
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Ceed
_computing_publication_material  'XCIF V6.12 (BrukerAXS, 2001).'

_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)+(0.0387P)²+1.6763P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8087
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_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
I1 I 1.03341(3) 0.11781(3) -0.47350(3) 0.04319(11) Uani 1 1 d . . .
I2 I 1.36892(3) 0.21044(3) 0.46146(2) 0.04309(11) Uani 1 1 d . . .
Fe1 Fe 0.90519(5) 0.26798(5) 0.03637(5) 0.02516(14) Uani 1 1 d . . .
N4 N 0.7293(3) 0.4034(3) -0.0327(3) 0.0274(8) Uani 1 1 d . . .
C25 C 0.8031(4) 0.6193(4) 0.0416(3) 0.0275(9) Uani 1 1 d . . .
H25 H 0.8669 0.6237 0.0809 0.033 Uiso 1 1 calc R . .
C27 C 0.6092(4) 0.7171(4) -0.0656(4) 0.0376(11) Uani 1 1 d . . .
H27 H 0.5402 0.7868 -0.0988 0.045 Uiso 1 1 calc R . .
O1 O 0.9731(3) 0.3032(3) -0.0967(2) 0.0335(7) Uani 1 1 d . . .
C17 C 1.1257(4) 0.1837(4) 0.1869(3) 0.0262(9) Uani 1 1 d . . .
N3 N 0.9121(3) 0.4052(3) 0.0811(3) 0.0244(7) Uani 1 1 d . . .
C30 C 0.5379(4) 0.4948(4) -0.1415(4) 0.0407(11) Uani 1 1 d . . .
H30 H 0.4763 0.4872 -0.1805 0.049 Uiso 1 1 calc R . .
C5 C 0.9639(4) 0.1280(4) -0.2578(3) 0.0318(10) Uani 1 1 d . . .
H5 H 0.9384 0.0660 -0.2562 0.038 Uiso 1 1 calc R . .
N2 N 0.8094(3) 0.2077(3) 0.1690(3) 0.0274(8) Uani 1 1 d . . .
C1 C 0.9861(4) 0.2607(4) -0.1740(3) 0.0295(9) Uani 1 1 d . . .
C23 C 0.9939(4) 0.3940(4) 0.1512(3) 0.0257(9) Uani 1 1 d . . .
H23 H 0.9851 0.4619 0.1674 0.031 Uiso 1 1 calc R . .
C3 C 1.0555(5) 0.2666(4) -0.3470(4) 0.0398(11) Uani 1 1 d . . .
H3 H 1.0922 0.3001 -0.4072 0.048 Uiso 1 1 calc R . .
C4 C 1.0159(4) 0.1761(4) -0.3437(4) 0.0342(10) Uani 1 1 d . . .
N1 N 0.8573(3) 0.1438(3) -0.0021(3) 0.0269(7) Uani 1 1 d . . .
C22 C 1.0957(4) 0.2903(4) 0.2063(3) 0.0263(9) Uani 1 1 d . . .
C29 C 0.5256(5) 0.6008(4) -0.1357(4) 0.0411(11) Uani 1 1 d . . .
H29 H 0.4555 0.6679 -0.1719 0.049 Uiso 1 1 calc R . .
C6 C 0.9468(4) 0.1679(4) -0.1711(3) 0.0282(9) Uani 1 1 d . . .
C18 C 1.2293(4) 0.0888(4) 0.2454(3) 0.0324(10) Uani 1 1 d . . .
H18 H 1.2518 0.0168 0.2329 0.039 Uiso 1 1 calc R . .
C12 C 0.7011(4) 0.0752(4) 0.2447(3) 0.0326(10) Uani 1 1 d . . .
C31 C 0.6423(4) 0.3985(4) -0.0894(3) 0.0341(10) Uani 1 1 d . . .
H31 H 0.6514 0.3253 -0.0949 0.041 Uiso 1 1 calc R . .
C15 C 0.7896(4) 0.2413(4) 0.2529(3) 0.0334(10) Uani 1 1 d . . .
H15 H 0.8195 0.2989 0.2566 0.040 Uiso 1 1 calc R . .
C9 C 0.7431(5) 0.0078(4) 0.0644(4) 0.0391(11) Uani 1 1 d . . .
H9 H 0.7555 -0.0151 0.0033 0.047 Uiso 1 1 calc R . .
C32 C 0.7188(4) 0.5092(3) -0.0256(3) 0.0266(9) Uani 1 1 d . . .
C21 C 1.1693(4) 0.2972(4) 0.2835(3) 0.0292(9) Uani 1 1 d . . .
H21 H 1.1493 0.3687 0.2966 0.035 Uiso 1 1 calc R . .
C7 C 0.8874(4) 0.1154(4) -0.0859(3) 0.0268(9) Uani 1 1 d . . .
H7 H 0.8676 0.0526 -0.0910 0.032 Uiso 1 1 calc R . .
C24 C 0.8138(4) 0.5135(3) 0.0349(3) 0.0259(9) Uani 1 1 d . . .
C14 C 0.7268(4) 0.1958(4) 0.3363(4) 0.0380(11) Uani 1 1 d . . .
H14 H 0.7140 0.2225 0.3952 0.046 Uiso 1 1 calc R . .
C26 C 0.7021(4) 0.7187(4) -0.0072(4) 0.0344(10) Uani 1 1 d . . .
H26 H 0.6971 0.7902 -0.0001 0.041 Uiso 1 1 calc R . .
C28 C 0.6160(4) 0.6110(4) -0.0764(4) 0.0323(10) Uani 1 1 d . . .
C8 C 0.7888(4) 0.0893(4) 0.0729(3) 0.0288(9) Uani 1 1 d . . .
C11 C 0.6575(5) -0.0087(4) 0.2323(4) 0.0416(12) Uani 1 1 d . . .
H11 H 0.6127 -0.0425 0.2856 0.050 Uiso 1 1 calc R . .
C13 C 0.6840(4) 0.1129(4) 0.3319(4) 0.0393(11) Uani 1 1 d . . .
H13 H 0.6422 0.0805 0.3887 0.047 Uiso 1 1 calc R . .
C20 C 1.2680(4) 0.2029(4) 0.3390(3) 0.0324(10) Uani 1 1 d . . .
C2 C 1.0410(5) 0.3066(4) -0.2634(4) 0.0381(11) Uani 1 1 d . . .
H2 H 1.0692 0.3673 -0.2660 0.046 Uiso 1 1 calc R . .
C19 C 1.2987(4) 0.0972(4) 0.3201(4) 0.0351(10) Uani 1 1 d . . .
H19 H 1.3680 0.0312 0.3593 0.042 Uiso 1 1 calc R . .
S1 S 0.46042(11) 0.76640(10) 0.26035(9) 0.0341(3) Uani 1 1 d . . .
F1 F 0.2972(3) 0.7597(3) 0.4004(3) 0.0731(10) Uani 1 1 d . . .
F2 F 0.4726(3) 0.6214(3) 0.4480(3) 0.0739(10) Uani 1 1 d . . .
C35 C 0.3912(5) 0.6882(5) 0.3653(4) 0.0472(13) Uani 1 1 d . . .
O3 O 0.3595(3) 0.8342(3) 0.1811(3) 0.0470(9) Uani 1 1 d . . .
O6 O 0.7869(3) 0.4918(3) 0.2833(3) 0.0538(9) Uani 1 1 d . . .
H6 H 0.7398 0.5622 0.2618 0.065 Uiso 1 1 calc R . .
O4 O 0.5022(4) 0.8299(3) 0.3095(3) 0.0608(11) Uani 1 1 d . . .
O5 O 0.5567(4) 0.6763(3) 0.2331(3) 0.0606(10) Uani 1 1 d . . .
F3 F 0.3448(5) 0.6228(4) 0.3354(3) 0.0999(15) Uani 1 1 d . . .
C10 C 0.6790(5) -0.0413(4) 0.1449(4) 0.0438(12) Uani 1 1 d . . .
H10 H 0.6499 -0.0985 0.1384 0.053 Uiso 1 1 calc R . .
C33 C 0.7766(6) 0.4441(5) 0.3920(4) 0.0564(15) Uani 1 1 d . . .
H33A H 0.8312 0.3608 0.4164 0.068 Uiso 1 1 calc R . .
H33B H 0.6889 0.4496 0.4030 0.068 Uiso 1 1 calc R . .
C34 C 0.8118(7) 0.5030(6) 0.4557(5) 0.0680(18) Uani 1 1 d . . .
H34A H 0.7544 0.5844 0.4353 0.102 Uiso 1 1 calc R . .
H34B H 0.8979 0.4995 0.4440 0.102 Uiso 1 1 calc R . .
H34C H 0.8066 0.4642 0.5303 0.102 Uiso 1 1 calc R . .
C16 C 0.7664(4) 0.1240(4) 0.1633(3) 0.0287(9) Uani 1 1 d . . .
O2 O 1.0626(3) 0.1712(2) 0.1152(2) 0.0319(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
I1 C4 2.094(4) . ?
I2 C20 2.104(4) . ?
Fe1 O1 1.907(3) . ?
Fe1 O2 1.908(3) . ?
Fe1 N3 2.094(3) . ?
Fe1 N1 2.101(3) . ?
Fe1 N2 2.139(3) . ?
Fe1 N4 2.142(4) . ?
N4 C31 1.314(5) . ?
N4 C32 1.379(5) . ?
C25 C26 1.375(6) . ?
C25 C24 1.375(5) . ?
C25 H25 0.9500 . ?
C27 C26 1.364(6) . ?
C27 C28 1.414(6) . ?
C27 H27 0.9500 . ?
O1 C1 1.308(5) . ?
C17 O2 1.316(5) . ?
C17 C18 1.400(6) . ?
C17 C22 1.415(6) . ?
N3 C23 1.298(5) . ?
N3 C24 1.415(5) . ?
C30 C29 1.369(7) . ?
C30 C31 1.388(6) . ?
C30 H30 0.9500 . ?
C5 C4 1.355(6) . ?
C5 C6 1.402(6) . ?
C5 H5 0.9500 . ?
N2 C15 1.319(5) . ?
N2 C16 1.376(5) . ?
C1 C2 1.396(6) . ?
C1 C6 1.429(6) . ?
C23 C22 1.426(6) . ?
C23 H23 0.9500 . ?
C3 C2 1.366(6) . ?
C3 C4 1.402(6) . ?
C3 H3 0.9500 . ?
N1 C7 1.292(5) . ?
N1 C8 1.422(5) . ?
C22 C21 1.414(6) . ?
C29 C28 1.406(6) . ?
C29 H29 0.9500 . ?
C6 C7 1.421(6) . ?
C18 C19 1.365(6) . ?
C18 H18 0.9500 . ?
C12 C13 1.392(7) . ?
C12 C16 1.413(6) . ?
C12 C11 1.417(6) . ?
C31 H31 0.9500 . ?
C15 C14 1.395(6) . ?
C15 H15 0.9500 . ?
C9 C8 1.383(6) . ?
C9 C10 1.399(6) . ?
C9 H9 0.9500 . ?
C32 C28 1.406(6) . ?
C32 C24 1.416(6) . ?
C21 C20 1.354(6) . ?
C21 H21 0.9500 . ?
C7 H7 0.9500 . ?
C14 C13 1.359(6) . ?
C14 H14 0.9500 . ?
C26 H26 0.9500 . ?
C8 C16 1.412(6) . ?
C11 C10 1.359(7) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C20 C19 1.400(6) . ?
C2 H2 0.9500 . ?
C19 H19 0.9500 . ?
S1 O3 1.423(3) . ?
S1 O4 1.424(3) . ?
S1 O5 1.427(4) . ?
S1 C35 1.800(5) . ?
F1 C35 1.328(6) . ?
F2 C35 1.324(6) . ?
C35 F3 1.321(6) . ?
O6 C33 1.413(6) . ?
O6 H6 0.8400 . ?
C10 H10 0.9500 . ?
C33 C34 1.474(8) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O2 95.66(13) . . ?
O1 Fe1 N3 98.59(12) . . ?
O2 Fe1 N3 88.92(13) . . ?
O1 Fe1 N1 88.83(12) . . ?
O2 Fe1 N1 100.25(13) . . ?
N3 Fe1 N1 167.63(13) . . ?
O1 Fe1 N2 166.23(12) . . ?
O2 Fe1 N2 90.05(13) . . ?
N3 Fe1 N2 94.03(13) . . ?
N1 Fe1 N2 77.81(13) . . ?
O1 Fe1 N4 89.31(14) . . ?
O2 Fe1 N4 166.53(12) . . ?
N3 Fe1 N4 77.94(13) . . ?
N1 Fe1 N4 92.34(13) . . ?
N2 Fe1 N4 87.94(13) . . ?
C31 N4 C32 119.1(4) . . ?
C31 N4 Fe1 127.5(3) . . ?
C32 N4 Fe1 112.9(3) . . ?
C26 C25 C24 121.4(4) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C26 C27 C28 119.6(4) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 H27 120.2 . . ?
C1 O1 Fe1 133.3(3) . . ?
O2 C17 C18 119.2(4) . . ?
O2 C17 C22 123.0(4) . . ?
C18 C17 C22 117.8(4) . . ?
C23 N3 C24 120.3(3) . . ?
C23 N3 Fe1 124.3(3) . . ?
C24 N3 Fe1 115.2(2) . . ?
C29 C30 C31 118.7(4) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C4 C5 C6 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C15 N2 C16 118.8(4) . . ?
C15 N2 Fe1 127.1(3) . . ?
C16 N2 Fe1 114.2(3) . . ?
O1 C1 C2 119.4(4) . . ?
O1 C1 C6 122.6(4) . . ?
C2 C1 C6 118.0(4) . . ?
N3 C23 C22 126.7(4) . . ?
N3 C23 H23 116.7 . . ?
C22 C23 H23 116.7 . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.2(4) . . ?
C5 C4 I1 120.0(3) . . ?
C3 C4 I1 119.8(3) . . ?
C7 N1 C8 120.6(3) . . ?
C7 N1 Fe1 124.5(3) . . ?
C8 N1 Fe1 114.9(3) . . ?
C17 C22 C21 119.6(4) . . ?
C17 C22 C23 123.6(4) . . ?
C21 C22 C23 116.8(4) . . ?
C30 C29 C28 120.4(4) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C5 C6 C7 117.6(4) . . ?
C5 C6 C1 118.9(4) . . ?
C7 C6 C1 123.5(4) . . ?
C19 C18 C17 121.6(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C13 C12 C16 117.7(4) . . ?
C13 C12 C11 124.4(4) . . ?
C16 C12 C11 117.9(4) . . ?
N4 C31 C30 123.3(4) . . ?
N4 C31 H31 118.4 . . ?
C30 C31 H31 118.4 . . ?
N2 C15 C14 122.9(4) . . ?
N2 C15 H15 118.6 . . ?
C14 C15 H15 118.6 . . ?
C8 C9 C10 120.6(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N4 C32 C28 121.1(4) . . ?
N4 C32 C24 118.5(4) . . ?
C28 C32 C24 120.4(4) . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
N1 C7 C6 127.0(4) . . ?
N1 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
C25 C24 N3 127.1(4) . . ?
C25 C24 C32 118.3(4) . . ?
N3 C24 C32 114.6(3) . . ?
C13 C14 C15 119.1(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C27 C26 C25 121.5(4) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C29 C28 C32 117.5(4) . . ?
C29 C28 C27 123.7(4) . . ?
C32 C28 C27 118.8(4) . . ?
C9 C8 C16 118.5(4) . . ?
C9 C8 N1 126.1(4) . . ?
C16 C8 N1 115.4(3) . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C14 C13 C12 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 I2 120.3(3) . . ?
C19 C20 I2 119.3(3) . . ?
C3 C2 C1 121.9(4) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C18 C19 C20 120.1(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
O3 S1 O4 115.6(2) . . ?
O3 S1 O5 113.6(2) . . ?
O4 S1 O5 115.8(3) . . ?
O3 S1 C35 103.7(2) . . ?
O4 S1 C35 102.3(2) . . ?
O5 S1 C35 103.4(2) . . ?
F3 C35 F2 108.5(5) . . ?
F3 C35 F1 106.7(5) . . ?
F2 C35 F1 105.6(4) . . ?
F3 C35 S1 112.2(4) . . ?
F2 C35 S1 111.9(4) . . ?
F1 C35 S1 111.7(4) . . ?
C33 O6 H6 109.5 . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
O6 C33 C34 113.0(5) . . ?
O6 C33 H33A 109.0 . . ?
C34 C33 H33A 109.0 . . ?
O6 C33 H33B 109.0 . . ?
C34 C33 H33B 109.0 . . ?
H33A C33 H33B 107.8 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N2 C16 C8 117.7(4) . . ?
N2 C16 C12 121.1(4) . . ?
C8 C16 C12 121.1(4) . . ?
C17 O2 Fe1 131.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.849
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.950
_refine_diff_density_max         1.713
_refine_diff_density_min         -1.130
_refine_diff_density_rms         0.119
####################################################################### 
# 
# 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_wp111-lt
_database_code_depnum_ccdc_archive 'CCDC 1519940'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C2 H6 O'
_chemical_formula_sum            'C35 H26 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         997.31

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'
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'
F F 0.0727 0.0534 '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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   11.5003(2)
_cell_length_b                   13.1342(3)
_cell_length_c                   13.5498(10)
_cell_angle_alpha                71.652(5)
_cell_angle_beta                 87.488(6)
_cell_angle_gamma                68.858(5)
_cell_volume                     1806.23(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    14691
_cell_measurement_theta_min      6.575
_cell_measurement_theta_max      72.0

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_F_000             974
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.579
_exptl_crystal_size_min          0.321
_exptl_absorpt_coefficient_mu    17.887
_shelx_estimated_absorpt_T_min   0.032
_shelx_estimated_absorpt_T_max   0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.303089
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku MM007 rotating anode'
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            25586
_diffrn_reflns_av_unetI/netI     0.0879
_diffrn_reflns_av_R_equivalents  0.0986
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.576
_diffrn_reflns_theta_max         72.113
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             6749
_reflns_number_gt                5630
_reflns_threshold_expression     'I > 2σ(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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX (Dolomanov, 2003) and SXGRAPH in WinGX v2013.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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/[σ²(Fo²)+(0.1293P)²+8.6618P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6749
_refine_ls_number_parameters     471
_refine_ls_number_restraints     311
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0841
_refine_ls_wR_factor_ref         0.2653
_refine_ls_wR_factor_gt          0.2191
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.192
_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_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
I2 I 0.53276(6) 0.61368(6) -0.46812(6) 0.0518(3) Uani 1 1 d . U . . .
I1 I 0.86601(6) 0.71022(7) 0.46387(6) 0.0521(3) Uani 1 1 d . . . . .
Fe1 Fe 0.40612(11) 0.76569(11) 0.03833(11) 0.0277(3) Uani 1 1 d . . . . .
S01 S 0.9615(2) 0.26485(19) 0.26155(19) 0.0390(5) Uani 1 1 d . . . . .
O1 O 0.5628(5) 0.6702(5) 0.1187(6) 0.0371(15) Uani 1 1 d . . . . .
O2 O 0.4756(6) 0.7966(5) -0.0946(4) 0.0335(14) Uani 1 1 d . . . . .
N1 N 0.4129(6) 0.9034(6) 0.0844(6) 0.0275(14) Uani 1 1 d . U . . .
O02 O 0.8621(8) 0.3328(7) 0.1825(7) 0.062(2) Uani 1 1 d . . . . .
N4 N 0.3082(6) 0.7058(6) 0.1689(5) 0.0289(14) Uani 1 1 d . U . . .
N2 N 0.2322(6) 0.9029(6) -0.0312(6) 0.0325(16) Uani 1 1 d . U . . .
F02 F 0.7969(7) 0.2610(9) 0.3983(7) 0.093(3) Uani 1 1 d . . . . .
F01 F 0.9698(8) 0.1221(7) 0.4471(7) 0.093(3) Uani 1 1 d . . . . .
O01 O 1.0042(9) 0.3265(8) 0.3100(7) 0.075(3) Uani 1 1 d . . . . .
C16 C 0.5947(7) 0.7902(8) 0.2088(7) 0.0325(17) Uani 1 1 d . U . . .
N3 N 0.3561(6) 0.6427(6) 0.0003(6) 0.0280(14) Uani 1 1 d . U . . .
C21 C 0.3166(7) 1.0115(7) 0.0371(6) 0.0228(15) Uani 1 1 d . U . . .
C29 C 0.2204(7) 1.0076(7) -0.0243(7) 0.0324(18) Uani 1 1 d . U . . .
F03 F 0.8410(12) 0.1278(10) 0.3349(9) 0.125(4) Uani 1 1 d . . . . .
C34 C 0.5175(8) 0.6717(7) -0.3356(6) 0.0386(13) Uani 1 1 d D U . . .
C28 C 0.1443(8) 0.8958(8) -0.0895(8) 0.038(2) Uani 1 1 d . U . . .
H28 H 0.1527 0.8246 -0.0964 0.046 Uiso 1 1 calc R U . . .
C31 C 0.4873(7) 0.7576(7) -0.1672(6) 0.0302(17) Uani 1 1 d D U . . .
C22 C 0.3072(8) 1.1174(7) 0.0447(7) 0.0314(17) Uani 1 1 d . U . . .
H22 H 0.3694 1.1215 0.0843 0.038 Uiso 1 1 calc R U . . .
O03 O 1.0559(8) 0.1752(8) 0.2328(8) 0.075(3) Uani 1 1 d . . . . .
C11 C 0.6250(7) 0.6833(7) 0.1904(7) 0.0333(18) Uani 1 1 d . U . . .
C41 C 0.2862(7) 0.5897(7) 0.0742(7) 0.0280(16) Uani 1 1 d . U . . .
C36 C 0.4474(7) 0.6651(7) -0.1662(6) 0.0279(16) Uani 1 1 d D U . . .
C17 C 0.4944(7) 0.8931(7) 0.1534(7) 0.0327(18) Uani 1 1 d . U . . .
H17 H 0.4866 0.9603 0.1686 0.039 Uiso 1 1 calc R U . . .
C49 C 0.2642(7) 0.6246(7) 0.1615(7) 0.0302(17) Uani 1 1 d . U . . .
C25 C 0.1192(8) 1.1092(8) -0.0770(8) 0.0362(19) Uani 1 1 d . U . . .
C37 C 0.3852(7) 0.6143(7) -0.0829(7) 0.0312(16) Uani 1 1 d . U . . .
H37 H 0.3632 0.5542 -0.0892 0.037 Uiso 1 1 calc R U . . .
C45 C 0.1981(8) 0.5768(8) 0.2439(8) 0.0390(19) Uani 1 1 d . U . . .
C32 C 0.5442(9) 0.8011(8) -0.2578(8) 0.045(2) Uani 1 1 d D U . . .
H32 H 0.5731 0.8605 -0.2612 0.055 Uiso 1 1 calc R U . . .
C23 C 0.2059(9) 1.2179(8) -0.0063(8) 0.043(2) Uani 1 1 d . U . . .
H23 H 0.2006 1.2889 -0.0004 0.052 Uiso 1 1 calc R U . . .
C26 C 0.0275(9) 1.0997(9) -0.1325(8) 0.044(2) Uani 1 1 d . U . . .
H26 H -0.0432 1.1652 -0.1650 0.053 Uiso 1 1 calc R U . . .
C42 C 0.2390(9) 0.5105(9) 0.0638(9) 0.047(2) Uani 1 1 d . U . . .
H42 H 0.2510 0.4882 0.0035 0.056 Uiso 1 1 calc R U . . .
C43 C 0.1724(10) 0.4626(9) 0.1441(9) 0.051(2) Uani 1 1 d . U . . .
H43 H 0.1416 0.4079 0.1368 0.061 Uiso 1 1 calc R U . . .
C35 C 0.4639(8) 0.6232(7) -0.2532(7) 0.0343(15) Uani 1 1 d D U . . .
H35 H 0.4380 0.5629 -0.2528 0.041 Uiso 1 1 calc R U . . .
C47 C 0.2246(9) 0.6967(9) 0.3365(8) 0.044(2) Uani 1 1 d . U . . .
H47 H 0.2137 0.7216 0.3953 0.053 Uiso 1 1 calc R U . . .
C27 C 0.0396(9) 0.9958(9) -0.1400(8) 0.044(2) Uani 1 1 d . U . . .
H27 H -0.0220 0.9901 -0.1790 0.053 Uiso 1 1 calc R U . . .
C48 C 0.2874(8) 0.7421(8) 0.2524(8) 0.040(2) Uani 1 1 d . U . . .
H48 H 0.3158 0.8000 0.2550 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7299(8) 0.5876(8) 0.2487(8) 0.042(2) Uani 1 1 d . U . . .
H12 H 0.7528 0.5168 0.2359 0.050 Uiso 1 1 calc R U . . .
C13 C 0.7978(8) 0.5975(8) 0.3232(8) 0.042(2) Uani 1 1 d . U . . .
H13 H 0.8663 0.5333 0.3618 0.050 Uiso 1 1 calc R U . . .
C33 C 0.5588(9) 0.7592(8) -0.3415(8) 0.0387(16) Uani 1 1 d . U . . .
H33 H 0.5960 0.7900 -0.4008 0.046 Uiso 1 1 calc R U . . .
C46 C 0.1800(9) 0.6155(9) 0.3301(8) 0.044(2) Uani 1 1 d . U . . .
H46 H 0.1364 0.5852 0.3848 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7662(8) 0.7015(8) 0.3421(8) 0.039(2) Uani 1 1 d . U . . .
C24 C 0.1133(9) 1.2135(8) -0.0653(8) 0.041(2) Uani 1 1 d . U . . .
H24 H 0.0452 1.2816 -0.0980 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6693(8) 0.7949(8) 0.2860(7) 0.0330(17) Uani 1 1 d . U . . .
H15 H 0.6511 0.8652 0.2987 0.040 Uiso 1 1 calc R U . . .
C01 C 0.8892(11) 0.1875(10) 0.3637(9) 0.053(3) Uani 1 1 d . U . . .
C44 C 0.1524(9) 0.4944(9) 0.2315(9) 0.048(2) Uani 1 1 d . U . . .
H44 H 0.1081 0.4616 0.2839 0.058 Uiso 1 1 calc R U . . .
C02 C 0.2823(15) 0.9411(12) 0.3916(11) 0.074(4) Uani 1 1 d D U . . .
H02A H 0.3361 0.8594 0.4127 0.089 Uiso 1 1 calc R U . . .
H02B H 0.1962 0.9459 0.4042 0.089 Uiso 1 1 calc R U . . .
O04 O 0.2892(8) 0.9915(8) 0.2847(7) 0.070(2) Uani 1 1 d . . . . .
H04 H 0.2296 1.0539 0.2626 0.105 Uiso 1 1 calc R U . . .
C03 C 0.3211(18) 0.9977(14) 0.4570(12) 0.090(5) Uani 1 1 d D U . . .
H03A H 0.4099 0.9829 0.4533 0.134 Uiso 1 1 calc R U . . .
H03B H 0.3041 0.9669 0.5288 0.134 Uiso 1 1 calc R U . . .
H03C H 0.2746 1.0801 0.4314 0.134 Uiso 1 1 calc R U . . .


_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
I2 C34 2.139(7) . ?
I1 C14 2.105(10) . ?
Fe1 O1 1.921(6) . ?
Fe1 O2 1.922(6) . ?
Fe1 N3 2.103(7) . ?
Fe1 N1 2.118(7) . ?
Fe1 N4 2.146(7) . ?
Fe1 N2 2.152(7) . ?
S01 O01 1.405(8) . ?
S01 O02 1.422(8) . ?
S01 O03 1.430(9) . ?
S01 C01 1.807(11) . ?
O1 C11 1.319(11) . ?
O2 C31 1.227(9) . ?
N1 C17 1.295(11) . ?
N1 C21 1.417(10) . ?
N4 C48 1.341(13) . ?
N4 C49 1.365(11) . ?
N2 C28 1.356(12) . ?
N2 C29 1.365(12) . ?
F02 C01 1.334(14) . ?
F01 C01 1.334(14) . ?
C16 C15 1.411(12) . ?
C16 C11 1.420(13) . ?
C16 C17 1.426(12) . ?
N3 C37 1.290(12) . ?
N3 C41 1.424(9) . ?
C21 C22 1.391(11) . ?
C21 C29 1.438(11) . ?
C29 C25 1.413(12) . ?
F03 C01 1.265(14) . ?
C34 C35 1.344(8) . ?
C34 C33 1.373(12) . ?
C28 C27 1.417(14) . ?
C28 H28 0.9400 . ?
C31 C32 1.421(12) . ?
C31 C36 1.442(11) . ?
C22 C23 1.402(13) . ?
C22 H22 0.9400 . ?
C11 C12 1.423(12) . ?
C41 C42 1.379(12) . ?
C41 C49 1.380(12) . ?
C36 C37 1.424(11) . ?
C36 C35 1.429(11) . ?
C17 H17 0.9400 . ?
C49 C45 1.431(11) . ?
C25 C26 1.385(13) . ?
C25 C24 1.407(14) . ?
C37 H37 0.9400 . ?
C45 C46 1.394(15) . ?
C45 C44 1.417(14) . ?
C32 C33 1.387(13) . ?
C32 H32 0.9400 . ?
C23 C24 1.387(14) . ?
C23 H23 0.9400 . ?
C26 C27 1.356(14) . ?
C26 H26 0.9400 . ?
C42 C43 1.417(13) . ?
C42 H42 0.9400 . ?
C43 C44 1.360(16) . ?
C43 H43 0.9400 . ?
C35 H35 0.9400 . ?
C47 C46 1.366(15) . ?
C47 C48 1.410(13) . ?
C47 H47 0.9400 . ?
C27 H27 0.9400 . ?
C48 H48 0.9400 . ?
C12 C13 1.368(15) . ?
C12 H12 0.9400 . ?
C13 C14 1.385(14) . ?
C13 H13 0.9400 . ?
C33 H33 0.9400 . ?
C46 H46 0.9400 . ?
C14 C15 1.351(13) . ?
C24 H24 0.9400 . ?
C15 H15 0.9400 . ?
C44 H44 0.9400 . ?
C02 O04 1.402(15) . ?
C02 C03 1.492(15) . ?
C02 H02A 0.9800 . ?
C02 H02B 0.9800 . ?
O04 H04 0.8300 . ?
C03 H03A 0.9700 . ?
C03 H03B 0.9700 . ?
C03 H03C 0.9700 . ?

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 O2 95.9(3) . . ?
O1 Fe1 N3 101.1(3) . . ?
O2 Fe1 N3 88.0(3) . . ?
O1 Fe1 N1 88.3(3) . . ?
O2 Fe1 N1 100.3(2) . . ?
N3 Fe1 N1 166.8(2) . . ?
O1 Fe1 N4 90.0(3) . . ?
O2 Fe1 N4 164.5(3) . . ?
N3 Fe1 N4 76.7(3) . . ?
N1 Fe1 N4 94.2(3) . . ?
O1 Fe1 N2 165.1(3) . . ?
O2 Fe1 N2 89.5(3) . . ?
N3 Fe1 N2 92.9(3) . . ?
N1 Fe1 N2 77.1(3) . . ?
N4 Fe1 N2 88.3(3) . . ?
O01 S01 O02 115.5(6) . . ?
O01 S01 O03 116.2(6) . . ?
O02 S01 O03 112.6(6) . . ?
O01 S01 C01 103.6(6) . . ?
O02 S01 C01 103.2(5) . . ?
O03 S01 C01 103.4(6) . . ?
C11 O1 Fe1 132.3(6) . . ?
C31 O2 Fe1 134.9(5) . . ?
C17 N1 C21 120.2(7) . . ?
C17 N1 Fe1 124.5(6) . . ?
C21 N1 Fe1 115.3(5) . . ?
C48 N4 C49 120.0(7) . . ?
C48 N4 Fe1 125.7(6) . . ?
C49 N4 Fe1 114.3(6) . . ?
C28 N2 C29 119.3(7) . . ?
C28 N2 Fe1 125.6(6) . . ?
C29 N2 Fe1 114.6(5) . . ?
C15 C16 C11 117.8(8) . . ?
C15 C16 C17 118.2(8) . . ?
C11 C16 C17 124.0(8) . . ?
C37 N3 C41 120.4(7) . . ?
C37 N3 Fe1 124.2(5) . . ?
C41 N3 Fe1 115.3(6) . . ?
C22 C21 N1 126.8(7) . . ?
C22 C21 C29 118.6(8) . . ?
N1 C21 C29 114.6(7) . . ?
N2 C29 C25 121.7(8) . . ?
N2 C29 C21 117.5(7) . . ?
C25 C29 C21 120.8(8) . . ?
C35 C34 C33 124.1(7) . . ?
C35 C34 I2 118.0(6) . . ?
C33 C34 I2 117.9(6) . . ?
N2 C28 C27 120.1(8) . . ?
N2 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
O2 C31 C32 120.9(7) . . ?
O2 C31 C36 123.1(7) . . ?
C32 C31 C36 116.0(6) . . ?
C21 C22 C23 120.7(8) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
O1 C11 C16 122.7(8) . . ?
O1 C11 C12 118.6(8) . . ?
C16 C11 C12 118.6(8) . . ?
C42 C41 C49 119.4(8) . . ?
C42 C41 N3 125.6(8) . . ?
C49 C41 N3 115.0(7) . . ?
C37 C36 C35 116.4(7) . . ?
C37 C36 C31 123.1(7) . . ?
C35 C36 C31 120.5(6) . . ?
N1 C17 C16 126.6(8) . . ?
N1 C17 H17 116.7 . . ?
C16 C17 H17 116.7 . . ?
N4 C49 C41 118.6(7) . . ?
N4 C49 C45 119.8(9) . . ?
C41 C49 C45 121.5(8) . . ?
C26 C25 C24 123.4(8) . . ?
C26 C25 C29 118.3(9) . . ?
C24 C25 C29 118.2(9) . . ?
N3 C37 C36 126.5(8) . . ?
N3 C37 H37 116.8 . . ?
C36 C37 H37 116.8 . . ?
C46 C45 C44 123.9(9) . . ?
C46 C45 C49 118.5(9) . . ?
C44 C45 C49 117.6(10) . . ?
C33 C32 C31 122.5(7) . . ?
C33 C32 H32 118.8 . . ?
C31 C32 H32 118.8 . . ?
C24 C23 C22 120.5(8) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C27 C26 C25 120.0(9) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C41 C42 C43 120.0(10) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C44 C43 C42 121.1(10) . . ?
C44 C43 H43 119.4 . . ?
C42 C43 H43 119.4 . . ?
C34 C35 C36 118.6(7) . . ?
C34 C35 H35 120.7 . . ?
C36 C35 H35 120.7 . . ?
C46 C47 C48 118.1(10) . . ?
C46 C47 H47 120.9 . . ?
C48 C47 H47 120.9 . . ?
C26 C27 C28 120.6(9) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
N4 C48 C47 122.5(9) . . ?
N4 C48 H48 118.7 . . ?
C47 C48 H48 118.7 . . ?
C13 C12 C11 120.6(9) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.4(9) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C34 C33 C32 118.5(8) . . ?
C34 C33 H33 120.8 . . ?
C32 C33 H33 120.8 . . ?
C47 C46 C45 121.0(9) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C15 C14 C13 120.4(9) . . ?
C15 C14 I1 120.4(7) . . ?
C13 C14 I1 119.1(7) . . ?
C23 C24 C25 121.2(8) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
C14 C15 C16 122.1(8) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
F03 C01 F01 110.4(11) . . ?
F03 C01 F02 106.3(11) . . ?
F01 C01 F02 104.6(10) . . ?
F03 C01 S01 113.7(9) . . ?
F01 C01 S01 110.9(8) . . ?
F02 C01 S01 110.4(8) . . ?
C43 C44 C45 120.2(9) . . ?
C43 C44 H44 119.9 . . ?
C45 C44 H44 119.9 . . ?
O04 C02 C03 112.7(12) . . ?
O04 C02 H02A 109.0 . . ?
C03 C02 H02A 109.0 . . ?
O04 C02 H02B 109.0 . . ?
C03 C02 H02B 109.0 . . ?
H02A C02 H02B 107.8 . . ?
C02 O04 H04 109.5 . . ?
C02 C03 H03A 109.5 . . ?
C02 C03 H03B 109.5 . . ?
H03A C03 H03B 109.5 . . ?
C02 C03 H03C 109.5 . . ?
H03A C03 H03C 109.5 . . ?
H03B C03 H03C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N1 C21 C22 10.1(12) . . . . ?
Fe1 N1 C21 C22 -172.4(6) . . . . ?
C17 N1 C21 C29 -169.8(7) . . . . ?
Fe1 N1 C21 C29 7.7(8) . . . . ?
C28 N2 C29 C25 -0.5(13) . . . . ?
Fe1 N2 C29 C25 172.0(7) . . . . ?
C28 N2 C29 C21 -179.1(8) . . . . ?
Fe1 N2 C29 C21 -6.7(10) . . . . ?
C22 C21 C29 N2 179.5(8) . . . . ?
N1 C21 C29 N2 -0.6(10) . . . . ?
C22 C21 C29 C25 0.9(12) . . . . ?
N1 C21 C29 C25 -179.2(8) . . . . ?
C29 N2 C28 C27 -1.8(13) . . . . ?
Fe1 N2 C28 C27 -173.4(7) . . . . ?
Fe1 O2 C31 C32 179.6(7) . . . . ?
Fe1 O2 C31 C36 -1.6(14) . . . . ?
N1 C21 C22 C23 -179.7(8) . . . . ?
C29 C21 C22 C23 0.2(12) . . . . ?
Fe1 O1 C11 C16 -13.0(12) . . . . ?
Fe1 O1 C11 C12 169.6(6) . . . . ?
C15 C16 C11 O1 -178.7(8) . . . . ?
C17 C16 C11 O1 0.7(13) . . . . ?
C15 C16 C11 C12 -1.3(12) . . . . ?
C17 C16 C11 C12 178.1(8) . . . . ?
C37 N3 C41 C42 -3.1(13) . . . . ?
Fe1 N3 C41 C42 177.2(7) . . . . ?
C37 N3 C41 C49 178.1(7) . . . . ?
Fe1 N3 C41 C49 -1.6(9) . . . . ?
O2 C31 C36 C37 3.2(13) . . . . ?
C32 C31 C36 C37 -178.0(8) . . . . ?
O2 C31 C36 C35 -179.8(8) . . . . ?
C32 C31 C36 C35 -0.9(12) . . . . ?
C21 N1 C17 C16 178.8(7) . . . . ?
Fe1 N1 C17 C16 1.5(12) . . . . ?
C15 C16 C17 N1 -176.2(8) . . . . ?
C11 C16 C17 N1 4.5(14) . . . . ?
C48 N4 C49 C41 179.5(7) . . . . ?
Fe1 N4 C49 C41 0.1(9) . . . . ?
C48 N4 C49 C45 -1.2(11) . . . . ?
Fe1 N4 C49 C45 179.4(6) . . . . ?
C42 C41 C49 N4 -177.9(8) . . . . ?
N3 C41 C49 N4 1.0(11) . . . . ?
C42 C41 C49 C45 2.8(13) . . . . ?
N3 C41 C49 C45 -178.3(7) . . . . ?
N2 C29 C25 C26 3.3(14) . . . . ?
C21 C29 C25 C26 -178.2(8) . . . . ?
N2 C29 C25 C24 179.5(8) . . . . ?
C21 C29 C25 C24 -1.9(13) . . . . ?
C41 N3 C37 C36 175.7(7) . . . . ?
Fe1 N3 C37 C36 -4.6(11) . . . . ?
C35 C36 C37 N3 -176.9(8) . . . . ?
C31 C36 C37 N3 0.3(13) . . . . ?
N4 C49 C45 C46 0.3(12) . . . . ?
C41 C49 C45 C46 179.5(8) . . . . ?
N4 C49 C45 C44 178.9(8) . . . . ?
C41 C49 C45 C44 -1.9(13) . . . . ?
O2 C31 C32 C33 -179.9(9) . . . . ?
C36 C31 C32 C33 1.2(14) . . . . ?
C21 C22 C23 C24 -0.1(14) . . . . ?
C24 C25 C26 C27 -179.7(10) . . . . ?
C29 C25 C26 C27 -3.7(16) . . . . ?
C49 C41 C42 C43 -2.3(14) . . . . ?
N3 C41 C42 C43 179.0(9) . . . . ?
C41 C42 C43 C44 0.9(16) . . . . ?
C33 C34 C35 C36 0.6(14) . . . . ?
I2 C34 C35 C36 -176.9(6) . . . . ?
C37 C36 C35 C34 177.3(8) . . . . ?
C31 C36 C35 C34 0.0(12) . . . . ?
C25 C26 C27 C28 1.4(17) . . . . ?
N2 C28 C27 C26 1.4(16) . . . . ?
C49 N4 C48 C47 2.2(13) . . . . ?
Fe1 N4 C48 C47 -178.5(7) . . . . ?
C46 C47 C48 N4 -2.2(14) . . . . ?
O1 C11 C12 C13 179.5(8) . . . . ?
C16 C11 C12 C13 2.0(13) . . . . ?
C11 C12 C13 C14 -0.8(14) . . . . ?
C35 C34 C33 C32 -0.3(15) . . . . ?
I2 C34 C33 C32 177.2(7) . . . . ?
C31 C32 C33 C34 -0.6(15) . . . . ?
C48 C47 C46 C45 1.2(15) . . . . ?
C44 C45 C46 C47 -178.8(10) . . . . ?
C49 C45 C46 C47 -0.3(14) . . . . ?
C12 C13 C14 C15 -1.2(14) . . . . ?
C12 C13 C14 I1 176.2(7) . . . . ?
C22 C23 C24 C25 -1.0(15) . . . . ?
C26 C25 C24 C23 178.0(10) . . . . ?
C29 C25 C24 C23 2.0(15) . . . . ?
C13 C14 C15 C16 1.9(14) . . . . ?
I1 C14 C15 C16 -175.4(6) . . . . ?
C11 C16 C15 C14 -0.6(13) . . . . ?
C17 C16 C15 C14 180.0(8) . . . . ?
O01 S01 C01 F03 178.3(11) . . . . ?
O02 S01 C01 F03 57.5(12) . . . . ?
O03 S01 C01 F03 -60.1(12) . . . . ?
O01 S01 C01 F01 -56.5(10) . . . . ?
O02 S01 C01 F01 -177.3(9) . . . . ?
O03 S01 C01 F01 65.1(10) . . . . ?
O01 S01 C01 F02 58.9(10) . . . . ?
O02 S01 C01 F02 -61.9(10) . . . . ?
O03 S01 C01 F02 -179.4(9) . . . . ?
C42 C43 C44 C45 0.0(16) . . . . ?
C46 C45 C44 C43 178.9(10) . . . . ?
C49 C45 C44 C43 0.4(14) . . . . ?

_refine_diff_density_max         1.758
_refine_diff_density_min         -3.047
_refine_diff_density_rms         0.240

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_wp111b
_database_code_depnum_ccdc_archive 'CCDC 1519941'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C35 H26 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         997.31

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'
O O 0.0492 0.0322 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   11.5289(9)
_cell_length_b                   13.1814(11)
_cell_length_c                   13.6233(12)
_cell_angle_alpha                71.947(5)
_cell_angle_beta                 87.644(6)
_cell_angle_gamma                68.871(5)
_cell_volume                     1830.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    1643
_cell_measurement_theta_min      6.6
_cell_measurement_theta_max      71.2

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             974
_exptl_absorpt_coefficient_mu    17.653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.230
_exptl_absorpt_correction_T_max  0.414
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_exptl_special_details           
; 
The measurement has been done at high temperature. The weak diffractions are then expected.
;

_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Rigaku MM007 rotating anode'
_diffrn_radiation_monochromator  'Rigaku VariMax-HF Confocal Optical System'
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20681
_diffrn_reflns_av_R_equivalents  0.1696
_diffrn_reflns_av_sigmaI/netI    0.1661
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.55
_diffrn_reflns_theta_max         65.08
_reflns_number_total             5882
_reflns_number_gt                3681
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'XCIF V6.12 (BrukerAXS, 2001).'

_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)+(0.0847P)²+0.5129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5882
_refine_ls_number_parameters     470
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0809
_refine_ls_wR_factor_ref         0.2282
_refine_ls_wR_factor_gt          0.1889
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.116
_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
I2 I 0.86317(6) -0.28920(6) 1.46554(6) 0.0827(3) Uani 1 1 d . . .
I1 I 0.53207(7) -0.39013(6) 0.53794(6) 0.0802(3) Uani 1 1 d . . .
Fe1 Fe 0.40640(11) -0.23689(10) 1.04160(11) 0.0510(4) Uani 1 1 d . . .
S1 S -0.0364(2) 0.26320(19) 1.2617(2) 0.0684(8) Uani 1 1 d . . .
N4 N 0.2336(6) -0.0988(5) 0.9700(6) 0.058(2) Uani 1 1 d . . .
N2 N 0.3052(6) -0.2930(5) 1.1705(6) 0.057(2) Uani 1 1 d . . .
C26 C 0.2124(9) 0.2116(7) 0.9941(8) 0.070(3) Uani 1 1 d . . .
H26 H 0.2096 0.2808 1.0003 0.084 Uiso 1 1 calc R . .
C9 C 0.2340(8) -0.4875(7) 1.0611(8) 0.066(3) Uani 1 1 d . . .
H9 H 0.2460 -0.5105 1.0022 0.079 Uiso 1 1 calc R . .
O1 O 0.4775(6) -0.2075(5) 0.9120(5) 0.0663(18) Uani 1 1 d . . .
F2 F -0.0334(8) 0.1229(6) 1.4475(7) 0.144(3) Uani 1 1 d . . .
O2 O 0.5614(5) -0.3320(4) 1.1221(5) 0.0571(17) Uani 1 1 d . . .
C12 C 0.1937(8) -0.4190(7) 1.2406(9) 0.060(2) Uani 1 1 d . . .
C25 C 0.3107(9) 0.1124(7) 1.0442(8) 0.064(3) Uani 1 1 d . . .
H25 H 0.3730 0.1163 1.0825 0.077 Uiso 1 1 calc R . .
C16 C 0.2612(7) -0.3743(7) 1.1628(8) 0.058(3) Uani 1 1 d . . .
C5 C 0.4651(7) -0.3776(7) 0.7502(7) 0.053(2) Uani 1 1 d . . .
H5 H 0.4386 -0.4368 0.7517 0.063 Uiso 1 1 calc R . .
C35 C -0.1094(13) 0.1887(10) 1.3659(12) 0.101(4) Uani 1 1 d . . .
O4 O 0.0071(8) 0.3238(7) 1.3110(6) 0.118(3) Uani 1 1 d . . .
C23 C 0.4951(7) -0.1103(7) 1.1548(7) 0.052(2) Uani 1 1 d . . .
H23 H 0.4875 -0.0439 1.1695 0.062 Uiso 1 1 calc R . .
N1 N 0.3540(6) -0.3588(5) 1.0010(6) 0.0491(18) Uani 1 1 d . . .
C8 C 0.2826(8) -0.4097(7) 1.0721(7) 0.052(2) Uani 1 1 d . . .
C7 C 0.3851(7) -0.3881(6) 0.9178(7) 0.049(2) Uani 1 1 d . . .
H7 H 0.3644 -0.4479 0.9115 0.059 Uiso 1 1 calc R . .
O3 O -0.1353(7) 0.3321(6) 1.1850(6) 0.103(3) Uani 1 1 d . . .
N3 N 0.4144(6) -0.0990(5) 1.0843(5) 0.0482(17) Uani 1 1 d . . .
C18 C 0.7275(8) -0.4118(7) 1.2510(7) 0.063(3) Uani 1 1 d . . .
H18 H 0.7489 -0.4821 1.2396 0.075 Uiso 1 1 calc R . .
C11 C 0.1449(8) -0.5007(7) 1.2265(9) 0.071(3) Uani 1 1 d . . .
H11 H 0.0993 -0.5320 1.2766 0.085 Uiso 1 1 calc R . .
C4 C 0.5185(7) -0.3347(7) 0.6656(6) 0.048(2) Uani 1 1 d U . .
F1 F -0.2008(8) 0.2617(8) 1.3980(7) 0.147(3) Uani 1 1 d . . .
C32 C 0.2233(7) 0.0051(6) 0.9773(6) 0.0434(19) Uani 1 1 d . . .
O5 O 0.0562(7) 0.1718(7) 1.2343(7) 0.116(3) Uani 1 1 d . . .
C1 C 0.4873(8) -0.2499(6) 0.8377(8) 0.052(2) Uani 1 1 d . . .
C6 C 0.4472(7) -0.3380(6) 0.8360(7) 0.043(2) Uani 1 1 d . . .
C21 C 0.6666(8) -0.2073(8) 1.2900(7) 0.062(3) Uani 1 1 d . . .
H21 H 0.6456 -0.1388 1.3048 0.074 Uiso 1 1 calc R . .
C15 C 0.2850(9) -0.2605(8) 1.2561(9) 0.066(3) Uani 1 1 d . . .
H15 H 0.3164 -0.2070 1.2629 0.080 Uiso 1 1 calc R . .
C22 C 0.5929(8) -0.2114(7) 1.2118(8) 0.057(2) Uani 1 1 d . . .
F3 F -0.1624(10) 0.1336(8) 1.3322(7) 0.175(4) Uani 1 1 d . . .
C29 C 0.0334(9) 0.0979(8) 0.8654(8) 0.080(3) Uani 1 1 d . . .
H29 H -0.0327 0.1637 0.8292 0.096 Uiso 1 1 calc R . .
C28 C 0.1229(8) 0.1058(6) 0.9254(8) 0.066(3) Uani 1 1 d . . .
C3 C 0.5606(9) -0.2469(8) 0.6648(8) 0.070(3) Uani 1 1 d . . .
H3 H 0.5977 -0.2146 0.6079 0.083 Uiso 1 1 calc R . .
C24 C 0.3184(7) 0.0085(7) 1.0385(7) 0.050(2) Uani 1 1 d . . .
C31 C 0.1456(8) -0.1039(7) 0.9146(8) 0.068(3) Uani 1 1 d . . .
H31 H 0.1514 -0.1750 0.9115 0.081 Uiso 1 1 calc R . .
C10 C 0.1667(9) -0.5311(8) 1.1391(9) 0.069(3) Uani 1 1 d . . .
H10 H 0.1350 -0.5839 1.1308 0.082 Uiso 1 1 calc R . .
C14 C 0.2201(8) -0.3034(8) 1.3329(8) 0.064(3) Uani 1 1 d . . .
H14 H 0.2060 -0.2769 1.3897 0.077 Uiso 1 1 calc R . .
C19 C 0.7959(8) -0.4014(8) 1.3240(8) 0.067(3) Uani 1 1 d . . .
H19 H 0.8641 -0.4644 1.3612 0.081 Uiso 1 1 calc R . .
O6 O 0.2886(7) -0.0069(7) 1.2878(7) 0.113(3) Uani 1 1 d . . .
H6 H 0.2417 0.0606 1.2699 0.135 Uiso 1 1 calc R . .
C13 C 0.1766(9) -0.3822(8) 1.3281(9) 0.074(3) Uani 1 1 d . . .
H13 H 0.1352 -0.4129 1.3825 0.089 Uiso 1 1 calc R . .
C20 C 0.7646(8) -0.2970(8) 1.3435(6) 0.053(2) Uani 1 1 d . . .
C27 C 0.1182(8) 0.2113(7) 0.9352(7) 0.054(2) Uani 1 1 d . . .
H27 H 0.0526 0.2792 0.9023 0.064 Uiso 1 1 calc R . .
C2 C 0.5459(9) -0.2092(8) 0.7502(9) 0.072(3) Uani 1 1 d . . .
H2 H 0.5771 -0.1531 0.7496 0.086 Uiso 1 1 calc R . .
C17 C 0.6241(7) -0.3171(7) 1.1923(7) 0.051(2) Uani 1 1 d . . .
C30 C 0.0426(9) -0.0054(8) 0.8597(8) 0.079(3) Uani 1 1 d . . .
H30 H -0.0173 -0.0118 0.8207 0.094 Uiso 1 1 calc R . .
C33 C 0.2874(16) -0.0553(11) 1.3934(11) 0.124(5) Uani 1 1 d . . .
H33B H 0.2030 -0.0504 1.4087 0.149 Uiso 1 1 calc R . .
H33A H 0.3398 -0.1359 1.4128 0.149 Uiso 1 1 calc R . .
C34 C 0.3274(17) -0.0060(13) 1.4539(13) 0.146(7) Uani 1 1 d . . .
H34A H 0.4144 -0.0196 1.4469 0.219 Uiso 1 1 calc R . .
H34B H 0.3150 -0.0392 1.5250 0.219 Uiso 1 1 calc R . .
H34C H 0.2806 0.0750 1.4320 0.219 Uiso 1 1 calc R . .


_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
I2 C20 2.101(7) . ?
I1 C4 2.065(8) . ?
Fe1 O1 1.904(7) . ?
Fe1 O2 1.913(5) . ?
Fe1 N3 2.106(6) . ?
Fe1 N1 2.128(7) . ?
Fe1 N2 2.155(8) . ?
Fe1 N4 2.163(7) . ?
S1 O3 1.406(7) . ?
S1 O4 1.411(6) . ?
S1 O5 1.431(7) . ?
S1 C35 1.823(14) . ?
N4 C31 1.321(9) . ?
N4 C32 1.366(9) . ?
N2 C15 1.346(12) . ?
N2 C16 1.371(10) . ?
C26 C27 1.379(12) . ?
C26 C25 1.379(12) . ?
C26 H26 0.9300 . ?
C9 C8 1.381(11) . ?
C9 C10 1.391(12) . ?
C9 H9 0.9300 . ?
O1 C1 1.282(9) . ?
F2 C35 1.300(13) . ?
O2 C17 1.323(9) . ?
C12 C16 1.397(13) . ?
C12 C13 1.403(13) . ?
C12 C11 1.444(12) . ?
C25 C24 1.367(11) . ?
C25 H25 0.9300 . ?
C16 C8 1.433(13) . ?
C5 C4 1.348(10) . ?
C5 C6 1.400(11) . ?
C5 H5 0.9300 . ?
C35 F3 1.289(13) . ?
C35 F1 1.311(14) . ?
C23 N3 1.301(9) . ?
C23 C22 1.413(11) . ?
C23 H23 0.9300 . ?
N1 C7 1.304(10) . ?
N1 C8 1.413(11) . ?
C7 C6 1.418(11) . ?
C7 H7 0.9300 . ?
N3 C24 1.414(9) . ?
C18 C19 1.362(11) . ?
C18 C17 1.416(10) . ?
C18 H18 0.9300 . ?
C11 C10 1.357(13) . ?
C11 H11 0.9300 . ?
C4 C3 1.404(11) . ?
C32 C28 1.407(11) . ?
C32 C24 1.426(10) . ?
C1 C2 1.402(12) . ?
C1 C6 1.403(9) . ?
C21 C20 1.333(11) . ?
C21 C22 1.415(11) . ?
C21 H21 0.9300 . ?
C15 C14 1.359(12) . ?
C15 H15 0.9300 . ?
C22 C17 1.415(11) . ?
C29 C30 1.355(12) . ?
C29 C28 1.394(11) . ?
C29 H29 0.9300 . ?
C28 C27 1.419(11) . ?
C3 C2 1.382(13) . ?
C3 H3 0.9300 . ?
C31 C30 1.419(11) . ?
C31 H31 0.9300 . ?
C10 H10 0.9300 . ?
C14 C13 1.325(12) . ?
C14 H14 0.9300 . ?
C19 C20 1.399(11) . ?
C19 H19 0.9300 . ?
O6 C33 1.383(13) . ?
O6 H6 0.8200 . ?
C13 H13 0.9300 . ?
C27 H27 0.9300 . ?
C2 H2 0.9300 . ?
C30 H30 0.9300 . ?
C33 C34 1.375(17) . ?
C33 H33B 0.9700 . ?
C33 H33A 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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 O2 95.6(3) . . ?
O1 Fe1 N3 98.8(3) . . ?
O2 Fe1 N3 88.7(2) . . ?
O1 Fe1 N1 88.0(3) . . ?
O2 Fe1 N1 101.8(2) . . ?
N3 Fe1 N1 167.0(3) . . ?
O1 Fe1 N2 165.2(2) . . ?
O2 Fe1 N2 90.5(3) . . ?
N3 Fe1 N2 94.9(3) . . ?
N1 Fe1 N2 77.5(3) . . ?
O1 Fe1 N4 89.3(3) . . ?
O2 Fe1 N4 165.3(2) . . ?
N3 Fe1 N4 76.8(2) . . ?
N1 Fe1 N4 92.2(2) . . ?
N2 Fe1 N4 88.2(3) . . ?
O3 S1 O4 114.9(5) . . ?
O3 S1 O5 114.1(5) . . ?
O4 S1 O5 116.8(5) . . ?
O3 S1 C35 103.6(6) . . ?
O4 S1 C35 101.6(6) . . ?
O5 S1 C35 103.3(6) . . ?
C31 N4 C32 118.7(7) . . ?
C31 N4 Fe1 126.9(6) . . ?
C32 N4 Fe1 114.1(5) . . ?
C15 N2 C16 118.4(9) . . ?
C15 N2 Fe1 127.8(6) . . ?
C16 N2 Fe1 113.8(7) . . ?
C27 C26 C25 121.9(8) . . ?
C27 C26 H26 119.0 . . ?
C25 C26 H26 119.0 . . ?
C8 C9 C10 119.2(10) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C1 O1 Fe1 132.7(5) . . ?
C17 O2 Fe1 132.0(5) . . ?
C16 C12 C13 118.4(9) . . ?
C16 C12 C11 118.2(10) . . ?
C13 C12 C11 123.4(10) . . ?
C24 C25 C26 121.2(8) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 H25 119.4 . . ?
N2 C16 C12 120.5(11) . . ?
N2 C16 C8 118.7(9) . . ?
C12 C16 C8 120.8(9) . . ?
C4 C5 C6 123.7(8) . . ?
C4 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
F3 C35 F2 112.0(11) . . ?
F3 C35 F1 104.4(12) . . ?
F2 C35 F1 105.6(13) . . ?
F3 C35 S1 110.2(11) . . ?
F2 C35 S1 113.3(9) . . ?
F1 C35 S1 111.0(8) . . ?
N3 C23 C22 127.8(7) . . ?
N3 C23 H23 116.1 . . ?
C22 C23 H23 116.1 . . ?
C7 N1 C8 120.4(7) . . ?
C7 N1 Fe1 124.2(6) . . ?
C8 N1 Fe1 115.4(6) . . ?
C9 C8 N1 126.1(9) . . ?
C9 C8 C16 119.4(9) . . ?
N1 C8 C16 114.5(7) . . ?
N1 C7 C6 126.6(8) . . ?
N1 C7 H7 116.7 . . ?
C6 C7 H7 116.7 . . ?
C23 N3 C24 120.1(6) . . ?
C23 N3 Fe1 123.6(5) . . ?
C24 N3 Fe1 116.0(5) . . ?
C19 C18 C17 121.0(8) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C10 C11 C12 119.0(10) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C5 C4 C3 117.8(8) . . ?
C5 C4 I1 121.7(6) . . ?
C3 C4 I1 120.5(7) . . ?
N4 C32 C28 121.2(7) . . ?
N4 C32 C24 117.9(7) . . ?
C28 C32 C24 120.9(7) . . ?
O1 C1 C2 119.1(7) . . ?
O1 C1 C6 125.9(8) . . ?
C2 C1 C6 115.0(8) . . ?
C5 C6 C1 120.1(8) . . ?
C5 C6 C7 117.5(7) . . ?
C1 C6 C7 122.3(8) . . ?
C20 C21 C22 123.1(8) . . ?
C20 C21 H21 118.5 . . ?
C22 C21 H21 118.5 . . ?
N2 C15 C14 122.1(9) . . ?
N2 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C23 C22 C17 123.1(7) . . ?
C23 C22 C21 119.2(8) . . ?
C17 C22 C21 117.7(7) . . ?
C30 C29 C28 120.0(8) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C28 C32 118.6(8) . . ?
C29 C28 C27 122.8(8) . . ?
C32 C28 C27 118.6(8) . . ?
C2 C3 C4 118.8(10) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C25 C24 N3 127.1(7) . . ?
C25 C24 C32 118.3(7) . . ?
N3 C24 C32 114.6(6) . . ?
N4 C31 C30 122.8(8) . . ?
N4 C31 H31 118.6 . . ?
C30 C31 H31 118.6 . . ?
C11 C10 C9 123.5(9) . . ?
C11 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
C13 C14 C15 121.2(11) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C18 C19 C20 120.6(8) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C33 O6 H6 109.5 . . ?
C14 C13 C12 119.5(10) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C21 C20 C19 119.3(7) . . ?
C21 C20 I2 121.4(7) . . ?
C19 C20 I2 119.1(6) . . ?
C26 C27 C28 119.0(8) . . ?
C26 C27 H27 120.5 . . ?
C28 C27 H27 120.5 . . ?
C3 C2 C1 124.5(8) . . ?
C3 C2 H2 117.8 . . ?
C1 C2 H2 117.8 . . ?
O2 C17 C22 123.3(7) . . ?
O2 C17 C18 118.4(7) . . ?
C22 C17 C18 118.4(7) . . ?
C29 C30 C31 118.5(8) . . ?
C29 C30 H30 120.7 . . ?
C31 C30 H30 120.7 . . ?
C34 C33 O6 115.2(13) . . ?
C34 C33 H33B 108.5 . . ?
O6 C33 H33B 108.5 . . ?
C34 C33 H33A 108.5 . . ?
O6 C33 H33A 108.5 . . ?
H33B C33 H33A 107.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

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
C25 H25 O1 0.93 2.45 3.268(10) 147.4 2_657
C18 H18 O3 0.93 2.65 3.552(12) 163.8 1_645
C31 H31 N1 0.93 2.67 3.226(10) 119.0 .
O6 H6 O5 0.82 2.08 2.794(11) 144.6 .
C30 H30 O5 0.93 2.63 3.378(12) 138.1 2_557
C33 H33A I1 0.97 3.23 4.173(14) 163.1 1_556

_diffrn_measured_fraction_theta_max 0.942
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.612
_refine_diff_density_min         -1.835
_refine_diff_density_rms         0.141
####################################################################### 
# 
# 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_wp133
_database_code_depnum_ccdc_archive 'CCDC 1519942'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C3 H8 O'
_chemical_formula_sum            'C36 H28 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         1011.33

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'
I I -0.4742 1.8119 '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'

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

_cell_length_a                   12.232(2)
_cell_length_b                   12.547(3)
_cell_length_c                   13.279(3)
_cell_angle_alpha                81.89(3)
_cell_angle_beta                 67.04(3)
_cell_angle_gamma                68.25(3)
_cell_volume                     1742.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.927
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             990
_exptl_absorpt_coefficient_mu    2.334
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9333
_exptl_absorpt_correction_T_max  0.9548
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 201r'
_diffrn_measurement_method       'scans in phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            73090
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         33.23
_reflns_number_total             11762
_reflns_number_gt                11056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blu-Ice (McPhillips et al, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-SEED
_computing_publication_material  'XCIF V6.12 (BrukerAXS, 2001).'

_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)+(0.0515P)²+6.9407P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11762
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_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
I1 I -0.00192(2) 0.83082(2) 0.63179(2) 0.03512(7) Uani 1 1 d . . .
I2 I 0.32180(3) 0.51566(2) 1.493753(19) 0.03469(7) Uani 1 1 d . . .
Fe1 Fe 0.31221(4) 0.36967(4) 0.96301(4) 0.01922(9) Uani 1 1 d . . .
O2 O 0.1989(2) 0.4366(2) 1.10142(19) 0.0242(4) Uani 1 1 d . . .
N1 N 0.1663(2) 0.3759(2) 0.9327(2) 0.0213(4) Uani 1 1 d . . .
C23 C 0.4649(3) 0.3886(3) 1.0765(3) 0.0214(5) Uani 1 1 d . . .
H23 H 0.5442 0.3838 1.0766 0.026 Uiso 1 1 calc R . .
O1 O 0.3186(2) 0.51078(19) 0.8953(2) 0.0238(4) Uani 1 1 d . . .
N4 N 0.4376(2) 0.2933(2) 0.8229(2) 0.0212(4) Uani 1 1 d . . .
S1 S 0.64356(8) 0.05497(8) 0.19150(7) 0.02790(15) Uani 1 1 d . . .
N3 N 0.4634(2) 0.3561(2) 0.9886(2) 0.0194(4) Uani 1 1 d . . .
F1 F 0.4031(3) 0.1576(3) 0.3065(2) 0.0471(6) Uani 1 1 d . . .
F3 F 0.5290(3) 0.1986(3) 0.3588(2) 0.0517(7) Uani 1 1 d . . .
F2 F 0.5058(3) 0.0350(3) 0.3972(2) 0.0520(7) Uani 1 1 d . . .
O3 O 0.6329(3) 0.1509(2) 0.1177(2) 0.0330(5) Uani 1 1 d . . .
C32 C 0.5599(3) 0.2779(2) 0.8098(2) 0.0209(5) Uani 1 1 d . . .
C7 C 0.1083(3) 0.4571(3) 0.8803(3) 0.0236(5) Uani 1 1 d . . .
H7 H 0.0357 0.4523 0.8735 0.028 Uiso 1 1 calc R . .
C15 C 0.3814(3) 0.1427(3) 1.0694(3) 0.0251(5) Uani 1 1 d . . .
H15 H 0.4515 0.1577 1.0706 0.030 Uiso 1 1 calc R . .
C24 C 0.5774(3) 0.3103(3) 0.8982(2) 0.0208(5) Uani 1 1 d . . .
O5 O 0.7554(3) 0.0175(3) 0.2196(3) 0.0446(7) Uani 1 1 d . . .
C22 C 0.3558(3) 0.4309(3) 1.1729(3) 0.0219(5) Uani 1 1 d . . .
C6 C 0.1455(3) 0.5534(3) 0.8319(3) 0.0229(5) Uani 1 1 d . . .
C1 C 0.2472(3) 0.5750(3) 0.8409(3) 0.0218(5) Uani 1 1 d . . .
C31 C 0.4174(3) 0.2623(3) 0.7424(3) 0.0255(6) Uani 1 1 d . . .
H31 H 0.3333 0.2715 0.7519 0.031 Uiso 1 1 calc R . .
C17 C 0.2302(3) 0.4522(3) 1.1807(3) 0.0232(5) Uani 1 1 d . . .
C5 C 0.0730(3) 0.6306(3) 0.7739(3) 0.0251(6) Uani 1 1 d . . .
H5 H 0.0030 0.6172 0.7705 0.030 Uiso 1 1 calc R . .
C20 C 0.2821(3) 0.4895(3) 1.3618(3) 0.0263(6) Uani 1 1 d . . .
O4 O 0.6116(3) -0.0361(2) 0.1694(2) 0.0347(5) Uani 1 1 d . . .
C25 C 0.6982(3) 0.2967(3) 0.8898(3) 0.0230(5) Uani 1 1 d . . .
H25 H 0.7111 0.3173 0.9493 0.028 Uiso 1 1 calc R . .
C21 C 0.3786(3) 0.4521(3) 1.2635(3) 0.0248(5) Uani 1 1 d . . .
H21 H 0.4628 0.4401 1.2559 0.030 Uiso 1 1 calc R . .
C27 C 0.7854(3) 0.2206(3) 0.7059(3) 0.0274(6) Uani 1 1 d . . .
H27 H 0.8565 0.1910 0.6410 0.033 Uiso 1 1 calc R . .
C4 C 0.1026(3) 0.7245(3) 0.7227(3) 0.0260(6) Uani 1 1 d . . .
C26 C 0.8021(3) 0.2521(3) 0.7929(3) 0.0263(6) Uani 1 1 d . . .
H26 H 0.8847 0.2437 0.7873 0.032 Uiso 1 1 calc R . .
C30 C 0.5160(3) 0.2160(3) 0.6429(3) 0.0294(6) Uani 1 1 d . . .
H30 H 0.4977 0.1949 0.5869 0.035 Uiso 1 1 calc R . .
C3 C 0.2032(3) 0.7469(3) 0.7301(3) 0.0282(6) Uani 1 1 d . . .
H3 H 0.2234 0.8123 0.6951 0.034 Uiso 1 1 calc R . .
C16 C 0.2041(3) 0.1975(3) 1.0230(3) 0.0235(5) Uani 1 1 d . . .
C2 C 0.2726(3) 0.6742(3) 0.7884(3) 0.0267(6) Uani 1 1 d . . .
H2 H 0.3398 0.6910 0.7936 0.032 Uiso 1 1 calc R . .
C28 C 0.6637(3) 0.2320(3) 0.7126(3) 0.0243(5) Uani 1 1 d . . .
C19 C 0.1570(3) 0.5107(3) 1.3712(3) 0.0297(6) Uani 1 1 d . . .
H19 H 0.0892 0.5370 1.4388 0.036 Uiso 1 1 calc R . .
C12 C 0.1787(3) 0.0965(3) 1.0677(3) 0.0269(6) Uani 1 1 d . . .
C18 C 0.1322(3) 0.4938(3) 1.2834(3) 0.0287(6) Uani 1 1 d . . .
H18 H 0.0469 0.5104 1.2914 0.034 Uiso 1 1 calc R . .
C29 C 0.6376(3) 0.2015(3) 0.6274(3) 0.0294(6) Uani 1 1 d . . .
H29 H 0.7042 0.1713 0.5603 0.035 Uiso 1 1 calc R . .
C8 C 0.1266(3) 0.2806(3) 0.9736(3) 0.0234(5) Uani 1 1 d . . .
C14 C 0.3626(3) 0.0400(3) 1.1150(3) 0.0292(6) Uani 1 1 d . . .
H14 H 0.4191 -0.0133 1.1464 0.035 Uiso 1 1 calc R . .
C13 C 0.2619(4) 0.0176(3) 1.1137(3) 0.0304(6) Uani 1 1 d . . .
H13 H 0.2485 -0.0518 1.1442 0.036 Uiso 1 1 calc R . .
C33 C 0.5138(4) 0.1152(4) 0.3199(3) 0.0348(7) Uani 1 1 d . . .
N2 N 0.3052(2) 0.2194(2) 1.0247(2) 0.0220(4) Uani 1 1 d . . .
C9 C 0.0225(3) 0.2639(3) 0.9700(3) 0.0285(6) Uani 1 1 d . . .
H9 H -0.0307 0.3197 0.9370 0.034 Uiso 1 1 calc R . .
C10 C -0.0043(3) 0.1639(3) 1.0152(3) 0.0321(7) Uani 1 1 d . . .
H10 H -0.0767 0.1534 1.0139 0.039 Uiso 1 1 calc R . .
C11 C 0.0727(2) 0.08150(17) 1.06122(18) 0.0319(7) Uani 1 1 d . . .
H11 H 0.0546 0.0134 1.0891 0.038 Uiso 1 1 calc R . .
C36 C 0.1465(2) 0.06881(17) 0.58017(18) 0.0420(10) Uani 1 1 d R . .
H36A H 0.2343 0.0158 0.5577 0.063 Uiso 1 1 calc R . .
H36B H 0.1032 0.0507 0.5400 0.063 Uiso 1 1 calc R . .
H36C H 0.1030 0.0610 0.6589 0.063 Uiso 1 1 calc R . .
O6 O 0.1472(2) 0.23171(17) 0.73187(18) 0.0640(10) Uani 1 1 d R . .
H6 H 0.1618 0.1610 0.7424 0.077 Uiso 1 1 calc R . .
C34 C 0.1449(2) 0.20301(17) 0.55287(18) 0.0482(10) Uani 1 1 d R . .
H34A H 0.2018 0.2058 0.4760 0.058 Uiso 1 1 calc R . .
H34B H 0.0582 0.2527 0.5585 0.058 Uiso 1 1 calc R . .
C35 C 0.1833(11) 0.2531(7) 0.6235(6) 0.096(3) Uani 1 1 d . . .
H35A H 0.2769 0.2274 0.5933 0.115 Uiso 1 1 calc R . .
H35B H 0.1520 0.3374 0.6146 0.115 Uiso 1 1 calc R . .


_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
I1 C4 2.087(3) . ?
I2 C20 2.088(3) . ?
Fe1 O1 1.883(2) . ?
Fe1 O2 1.895(2) . ?
Fe1 N1 1.950(2) . ?
Fe1 N3 1.950(2) . ?
Fe1 N2 1.966(3) . ?
Fe1 N4 1.980(3) . ?
O2 C17 1.312(4) . ?
N1 C7 1.295(4) . ?
N1 C8 1.415(4) . ?
C23 N3 1.298(4) . ?
C23 C22 1.427(4) . ?
C23 H23 0.9500 . ?
O1 C1 1.319(4) . ?
N4 C31 1.323(4) . ?
N4 C32 1.378(4) . ?
S1 O4 1.436(3) . ?
S1 O3 1.442(3) . ?
S1 O5 1.451(3) . ?
S1 C33 1.833(4) . ?
N3 C24 1.418(4) . ?
F1 C33 1.332(5) . ?
F3 C33 1.329(5) . ?
F2 C33 1.335(5) . ?
C32 C24 1.410(4) . ?
C32 C28 1.414(4) . ?
C7 C6 1.428(5) . ?
C7 H7 0.9500 . ?
C15 N2 1.323(4) . ?
C15 C14 1.404(5) . ?
C15 H15 0.9500 . ?
C24 C25 1.383(4) . ?
C22 C21 1.414(4) . ?
C22 C17 1.422(4) . ?
C6 C5 1.415(4) . ?
C6 C1 1.418(4) . ?
C1 C2 1.415(4) . ?
C31 C30 1.411(5) . ?
C31 H31 0.9500 . ?
C17 C18 1.424(5) . ?
C5 C4 1.371(5) . ?
C5 H5 0.9500 . ?
C20 C21 1.370(5) . ?
C20 C19 1.409(5) . ?
C25 C26 1.408(4) . ?
C25 H25 0.9500 . ?
C21 H21 0.9500 . ?
C27 C26 1.380(5) . ?
C27 C28 1.410(4) . ?
C27 H27 0.9500 . ?
C4 C3 1.401(5) . ?
C26 H26 0.9500 . ?
C30 C29 1.363(5) . ?
C30 H30 0.9500 . ?
C3 C2 1.376(5) . ?
C3 H3 0.9500 . ?
C16 N2 1.372(4) . ?
C16 C8 1.406(5) . ?
C16 C12 1.410(4) . ?
C2 H2 0.9500 . ?
C28 C29 1.422(5) . ?
C19 C18 1.375(5) . ?
C19 H19 0.9500 . ?
C12 C13 1.400(5) . ?
C12 C11 1.412(4) . ?
C18 H18 0.9500 . ?
C29 H29 0.9500 . ?
C8 C9 1.384(4) . ?
C14 C13 1.367(5) . ?
C14 H14 0.9500 . ?
C13 H13 0.9500 . ?
C9 C10 1.407(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C36 C34 1.6661 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
O6 C35 1.349(7) . ?
O6 H6 0.8400 . ?
C34 C35 1.491(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 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 O2 94.24(11) . . ?
O1 Fe1 N1 94.76(11) . . ?
O2 Fe1 N1 88.23(10) . . ?
O1 Fe1 N3 86.67(10) . . ?
O2 Fe1 N3 94.34(10) . . ?
N1 Fe1 N3 176.96(11) . . ?
O1 Fe1 N2 176.16(11) . . ?
O2 Fe1 N2 88.67(11) . . ?
N1 Fe1 N2 82.81(11) . . ?
N3 Fe1 N2 95.62(11) . . ?
O1 Fe1 N4 87.91(11) . . ?
O2 Fe1 N4 176.46(11) . . ?
N1 Fe1 N4 94.40(11) . . ?
N3 Fe1 N4 82.96(11) . . ?
N2 Fe1 N4 89.32(11) . . ?
C17 O2 Fe1 126.2(2) . . ?
C7 N1 C8 121.0(3) . . ?
C7 N1 Fe1 125.4(2) . . ?
C8 N1 Fe1 113.6(2) . . ?
N3 C23 C22 124.6(3) . . ?
N3 C23 H23 117.7 . . ?
C22 C23 H23 117.7 . . ?
C1 O1 Fe1 126.03(19) . . ?
C31 N4 C32 118.6(3) . . ?
C31 N4 Fe1 128.7(2) . . ?
C32 N4 Fe1 112.6(2) . . ?
O4 S1 O3 115.30(17) . . ?
O4 S1 O5 114.8(2) . . ?
O3 S1 O5 115.22(19) . . ?
O4 S1 C33 102.42(18) . . ?
O3 S1 C33 102.98(18) . . ?
O5 S1 C33 103.6(2) . . ?
C23 N3 C24 120.7(2) . . ?
C23 N3 Fe1 125.6(2) . . ?
C24 N3 Fe1 113.66(19) . . ?
N4 C32 C24 116.8(3) . . ?
N4 C32 C28 122.1(3) . . ?
C24 C32 C28 121.1(3) . . ?
N1 C7 C6 124.7(3) . . ?
N1 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
N2 C15 C14 122.5(3) . . ?
N2 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C25 C24 C32 119.4(3) . . ?
C25 C24 N3 126.9(3) . . ?
C32 C24 N3 113.7(2) . . ?
C21 C22 C17 120.4(3) . . ?
C21 C22 C23 116.0(3) . . ?
C17 C22 C23 123.6(3) . . ?
C5 C6 C1 120.0(3) . . ?
C5 C6 C7 116.3(3) . . ?
C1 C6 C7 123.8(3) . . ?
O1 C1 C2 117.8(3) . . ?
O1 C1 C6 125.1(3) . . ?
C2 C1 C6 117.2(3) . . ?
N4 C31 C30 122.6(3) . . ?
N4 C31 H31 118.7 . . ?
C30 C31 H31 118.7 . . ?
O2 C17 C22 125.1(3) . . ?
O2 C17 C18 118.5(3) . . ?
C22 C17 C18 116.4(3) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C21 C20 C19 118.9(3) . . ?
C21 C20 I2 119.9(2) . . ?
C19 C20 I2 121.2(2) . . ?
C24 C25 C26 120.0(3) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C20 C21 C22 121.5(3) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C26 C27 C28 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 I1 119.1(2) . . ?
C3 C4 I1 120.9(3) . . ?
C27 C26 C25 120.9(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C29 C30 C31 119.9(3) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
N2 C16 C8 116.7(3) . . ?
N2 C16 C12 122.2(3) . . ?
C8 C16 C12 121.1(3) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C27 C28 C32 118.2(3) . . ?
C27 C28 C29 124.4(3) . . ?
C32 C28 C29 117.4(3) . . ?
C18 C19 C20 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C13 C12 C16 117.3(3) . . ?
C13 C12 C11 124.8(3) . . ?
C16 C12 C11 117.9(3) . . ?
C19 C18 C17 122.2(3) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C30 C29 C28 119.4(3) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C9 C8 C16 119.5(3) . . ?
C9 C8 N1 126.9(3) . . ?
C16 C8 N1 113.5(3) . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
F3 C33 F1 108.0(4) . . ?
F3 C33 F2 106.9(3) . . ?
F1 C33 F2 107.4(3) . . ?
F3 C33 S1 112.3(3) . . ?
F1 C33 S1 111.0(3) . . ?
F2 C33 S1 111.0(3) . . ?
C15 N2 C16 118.6(3) . . ?
C15 N2 Fe1 128.2(2) . . ?
C16 N2 Fe1 113.1(2) . . ?
C8 C9 C10 119.7(3) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 O6 H6 109.5 . . ?
C35 C34 C36 116.6(3) . . ?
C35 C34 H34A 108.1 . . ?
C36 C34 H34A 108.1 . . ?
C35 C34 H34B 108.1 . . ?
C36 C34 H34B 108.1 . . ?
H34A C34 H34B 107.3 . . ?
O6 C35 C34 120.4(5) . . ?
O6 C35 H35A 107.2 . . ?
C34 C35 H35A 107.2 . . ?
O6 C35 H35B 107.2 . . ?
C34 C35 H35B 107.2 . . ?
H35A C35 H35B 106.9 . . ?

_diffrn_measured_fraction_theta_max 0.878
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         2.441
_refine_diff_density_min         -2.104
_refine_diff_density_rms         0.147
####################################################################### 
# 
# 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_wp113-lt
_database_code_depnum_ccdc_archive 'CCDC 1519946'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C3 H6 O'
_chemical_formula_sum            'C36 H26 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         1009.32

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'
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'
F F 0.0727 0.0534 '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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.3759(4)
_cell_length_b                   12.8053(5)
_cell_length_c                   13.8091(10)
_cell_angle_alpha                79.080(6)
_cell_angle_beta                 76.267(5)
_cell_angle_gamma                86.609(6)
_cell_volume                     1749.85(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    137(2)
_cell_measurement_reflns_used    3966
_cell_measurement_theta_min      6.71
_cell_measurement_theta_max      71.98

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_F_000             986
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.328
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    18.474
_shelx_estimated_absorpt_T_min   0.016
_shelx_estimated_absorpt_T_max   0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.187137
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      137(2)
_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku MM007 rotating anode'
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            24183
_diffrn_reflns_av_unetI/netI     0.0836
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.711
_diffrn_reflns_theta_max         71.987
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.940
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             6466
_reflns_number_gt                5485
_reflns_threshold_expression     'I > 2σ(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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX (Dolomanov, 2003) and SXGRAPH in WinGX v2013.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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/[σ²(Fo²)+(0.1071P)²+10.8507P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6466
_refine_ls_number_parameters     480
_refine_ls_number_restraints     127
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.2451
_refine_ls_wR_factor_gt          0.2156
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.242
_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_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
I1 I 1.34164(7) 0.06610(6) 0.06926(5) 0.0506(3) Uani 1 1 d . . . . .
I2 I 1.20509(7) 0.38389(6) 0.90750(5) 0.0548(3) Uani 1 1 d . . . . .
Fe1 Fe 0.86416(12) 0.24752(10) 0.51810(9) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.9759(6) 0.1834(5) 0.6060(4) 0.0356(14) Uani 1 1 d . . . . .
N4 N 0.7413(7) 0.3195(6) 0.4350(5) 0.0310(15) Uani 1 1 d . . . . .
O1 O 1.0136(6) 0.2964(5) 0.4096(4) 0.0392(15) Uani 1 1 d . . . . .
S01 S 0.6558(9) 0.4491(8) 0.8926(6) 0.170(3) Uani 1 1 d D U . . .
N3 N 0.8582(6) 0.3860(6) 0.5579(5) 0.0287(15) Uani 1 1 d . . . . .
N2 N 0.7070(7) 0.1901(6) 0.6228(5) 0.0332(16) Uani 1 1 d . . . . .
N1 N 0.8606(7) 0.1107(6) 0.4761(5) 0.0325(16) Uani 1 1 d . . . . .
O01 O 0.6637(11) 0.4432(9) 0.7970(8) 0.095(3) Uani 1 1 d D U . . .
C36 C 0.9939(8) 0.3378(7) 0.6815(6) 0.0333(19) Uani 1 1 d . . . . .
C16 C 1.0580(9) 0.1353(7) 0.3385(7) 0.0333(19) Uani 1 1 d . . . . .
C29 C 0.6681(8) 0.0945(7) 0.6101(6) 0.0295(17) Uani 1 1 d . . . . .
C45 C 0.6355(8) 0.4902(8) 0.3864(7) 0.039(2) Uani 1 1 d . . . . .
O04 O 0.7900(9) 0.1117(8) 0.2158(7) 0.072(3) Uani 1 1 d . . . . .
C26 C 0.4758(9) 0.0937(8) 0.7497(7) 0.044(2) Uani 1 1 d . . . . .
H26 H 0.3951 0.0644 0.7917 0.053 Uiso 1 1 calc R U . . .
C21 C 0.7505(9) 0.0470(8) 0.5316(7) 0.038(2) Uani 1 1 d . . . . .
C41 C 0.7818(8) 0.4635(8) 0.5075(6) 0.033(2) Uani 1 1 d . . . . .
C42 C 0.7640(9) 0.5707(7) 0.5147(7) 0.036(2) Uani 1 1 d . . . . .
H42 H 0.8055 0.5988 0.5584 0.043 Uiso 1 1 calc R U . . .
C25 C 0.5525(9) 0.0412(8) 0.6713(7) 0.040(2) Uani 1 1 d . . . . .
C32 C 1.0911(9) 0.1677(8) 0.7356(7) 0.038(2) Uani 1 1 d . . . . .
H32 H 1.1061 0.0944 0.7326 0.046 Uiso 1 1 calc R U . . .
C35 C 1.0478(9) 0.3796(9) 0.7492(7) 0.041(2) Uani 1 1 d . . . . .
H35 H 1.0336 0.4527 0.7536 0.049 Uiso 1 1 calc R U . . .
C24 C 0.5219(11) -0.0570(10) 0.6525(8) 0.055(3) Uani 1 1 d . . . . .
H24 H 0.4449 -0.0934 0.6931 0.066 Uiso 1 1 calc R U . . .
C37 C 0.9184(8) 0.4098(7) 0.6220(6) 0.0316(18) Uani 1 1 d . . . . .
H37 H 0.9124 0.4818 0.6310 0.038 Uiso 1 1 calc R U . . .
C47 C 0.5987(9) 0.3391(9) 0.3177(7) 0.043(2) Uani 1 1 d . . . . .
H47 H 0.5596 0.3073 0.2750 0.051 Uiso 1 1 calc R U . . .
C17 C 0.9494(9) 0.0750(8) 0.4066(7) 0.037(2) Uani 1 1 d . . . . .
H17 H 0.9424 0.0032 0.4000 0.044 Uiso 1 1 calc R U . . .
C49 C 0.7187(8) 0.4231(7) 0.4420(6) 0.0302(18) Uani 1 1 d . . . . .
C48 C 0.6823(9) 0.2779(9) 0.3765(7) 0.042(2) Uani 1 1 d . . . . .
H48 H 0.6960 0.2045 0.3734 0.050 Uiso 1 1 calc R U . . .
C11 C 1.0825(8) 0.2411(8) 0.3430(6) 0.036(2) Uani 1 1 d . . . . .
C31 C 1.0162(8) 0.2303(8) 0.6710(7) 0.035(2) Uani 1 1 d . . . . .
C15 C 1.1356(9) 0.0856(8) 0.2619(7) 0.037(2) Uani 1 1 d . . . . .
H15 H 1.1188 0.0137 0.2611 0.045 Uiso 1 1 calc R U . . .
C44 C 0.6217(10) 0.5983(8) 0.3962(7) 0.045(2) Uani 1 1 d . . . . .
H44 H 0.5676 0.6444 0.3595 0.054 Uiso 1 1 calc R U . . .
C33 C 1.1426(9) 0.2115(9) 0.8028(7) 0.045(2) Uani 1 1 d . . . . .
H33 H 1.1932 0.1680 0.8444 0.054 Uiso 1 1 calc R U . . .
C28 C 0.6337(9) 0.2341(7) 0.6979(7) 0.0355(19) Uani 1 1 d . . . . .
H28 H 0.6591 0.3006 0.7082 0.043 Uiso 1 1 calc R U . . .
C43 C 0.6853(10) 0.6381(8) 0.4579(7) 0.042(2) Uani 1 1 d . . . . .
H43 H 0.6761 0.7114 0.4623 0.051 Uiso 1 1 calc R U . . .
C14 C 1.2364(9) 0.1384(8) 0.1870(7) 0.039(2) Uani 1 1 d . . . . .
C46 C 0.5756(9) 0.4445(9) 0.3237(7) 0.042(2) Uani 1 1 d . . . . .
H46 H 0.5195 0.4863 0.2856 0.050 Uiso 1 1 calc R U . . .
C22 C 0.7155(12) -0.0478(10) 0.5155(9) 0.056(3) Uani 1 1 d . . . . .
H22 H 0.7689 -0.0790 0.4621 0.067 Uiso 1 1 calc R U . . .
C12 C 1.1885(10) 0.2936(9) 0.2665(7) 0.046(2) Uani 1 1 d . . . . .
H12 H 1.2079 0.3647 0.2680 0.055 Uiso 1 1 calc R U . . .
C27 C 0.5206(10) 0.1849(9) 0.7620(7) 0.044(2) Uani 1 1 d . . . . .
H27 H 0.4734 0.2175 0.8167 0.053 Uiso 1 1 calc R U . . .
C13 C 1.2630(9) 0.2449(8) 0.1912(7) 0.042(2) Uani 1 1 d . . . . .
H13 H 1.3327 0.2823 0.1416 0.050 Uiso 1 1 calc R U . . .
C02 C 0.8658(10) 0.1618(10) 0.1456(9) 0.053(3) Uani 1 1 d . . . . .
C34 C 1.1210(9) 0.3171(7) 0.8098(6) 0.0329(18) Uani 1 1 d . . . . .
C23 C 0.6007(12) -0.1003(11) 0.5774(10) 0.068(4) Uani 1 1 d . . . . .
H23 H 0.5788 -0.1672 0.5658 0.081 Uiso 1 1 calc R U . . .
C03 C 0.9314(15) 0.1091(14) 0.0577(9) 0.080(4) Uani 1 1 d . . . . .
H03A H 1.0272 0.1209 0.0411 0.120 Uiso 1 1 calc R U . . .
H03B H 0.8953 0.1395 -0.0012 0.120 Uiso 1 1 calc R U . . .
H03C H 0.9145 0.0326 0.0758 0.120 Uiso 1 1 calc R U . . .
C04 C 0.9072(14) 0.2709(12) 0.1401(11) 0.075(4) Uani 1 1 d . . . . .
H04A H 0.8816 0.2898 0.2077 0.113 Uiso 1 1 calc R U . . .
H04B H 0.8640 0.3202 0.0937 0.113 Uiso 1 1 calc R U . . .
H04C H 1.0038 0.2756 0.1153 0.113 Uiso 1 1 calc R U . . .
F01 F 0.6966(18) 0.2557(12) 0.9357(13) 0.197(5) Uani 1 1 d D U . . .
F02 F 0.6229(19) 0.3340(14) 1.0634(11) 0.210(6) Uani 1 1 d D U . . .
O02 O 0.7804(17) 0.4693(16) 0.9181(13) 0.195(6) Uani 1 1 d D U . . .
O03 O 0.559(2) 0.5218(15) 0.9387(14) 0.239(7) Uani 1 1 d D U . . .
F03 F 0.4916(17) 0.3130(16) 0.9665(15) 0.238(6) Uani 1 1 d D U . . .
C01 C 0.6178(19) 0.335(3) 0.9652(19) 0.187(4) Uani 1 1 d D U . . .


_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
I1 C14 2.074(9) . ?
I2 C34 2.096(9) . ?
Fe1 O2 1.916(6) . ?
Fe1 O1 1.923(6) . ?
Fe1 N3 1.947(7) . ?
Fe1 N1 1.952(8) . ?
Fe1 N2 1.977(7) . ?
Fe1 N4 1.987(7) . ?
O2 C31 1.324(11) . ?
N4 C48 1.322(12) . ?
N4 C49 1.351(11) . ?
O1 C11 1.316(12) . ?
S01 O01 1.320(11) . ?
S01 O03 1.444(14) . ?
S01 O02 1.467(14) . ?
S01 C01 1.62(4) . ?
N3 C37 1.286(11) . ?
N3 C41 1.418(11) . ?
N2 C28 1.330(12) . ?
N2 C29 1.366(11) . ?
N1 C17 1.294(12) . ?
N1 C21 1.419(10) . ?
C36 C35 1.395(13) . ?
C36 C31 1.411(13) . ?
C36 C37 1.439(12) . ?
C16 C15 1.401(13) . ?
C16 C11 1.409(13) . ?
C16 C17 1.440(11) . ?
C29 C25 1.420(11) . ?
C29 C21 1.422(13) . ?
C45 C44 1.412(15) . ?
C45 C46 1.403(14) . ?
C45 C49 1.432(12) . ?
O04 C02 1.196(13) . ?
C26 C27 1.337(15) . ?
C26 C25 1.435(15) . ?
C26 H26 0.9500 . ?
C21 C22 1.360(15) . ?
C41 C42 1.393(13) . ?
C41 C49 1.419(12) . ?
C42 C43 1.411(13) . ?
C42 H42 0.9500 . ?
C25 C24 1.399(15) . ?
C32 C33 1.390(14) . ?
C32 C31 1.423(12) . ?
C32 H32 0.9500 . ?
C35 C34 1.376(13) . ?
C35 H35 0.9500 . ?
C24 C23 1.347(17) . ?
C24 H24 0.9500 . ?
C37 H37 0.9500 . ?
C47 C46 1.371(15) . ?
C47 C48 1.428(13) . ?
C47 H47 0.9500 . ?
C17 H17 0.9500 . ?
C48 H48 0.9500 . ?
C11 C12 1.429(11) . ?
C15 C14 1.387(13) . ?
C15 H15 0.9500 . ?
C44 C43 1.375(15) . ?
C44 H44 0.9500 . ?
C33 C34 1.375(14) . ?
C33 H33 0.9500 . ?
C28 C27 1.393(12) . ?
C28 H28 0.9500 . ?
C43 H43 0.9500 . ?
C14 C13 1.422(14) . ?
C46 H46 0.9500 . ?
C22 C23 1.412(13) . ?
C22 H22 0.9500 . ?
C12 C13 1.369(14) . ?
C12 H12 0.9500 . ?
C27 H27 0.9500 . ?
C13 H13 0.9500 . ?
C02 C04 1.469(18) . ?
C02 C03 1.502(18) . ?
C23 H23 0.9500 . ?
C03 H03A 0.9800 . ?
C03 H03B 0.9800 . ?
C03 H03C 0.9800 . ?
C04 H04A 0.9800 . ?
C04 H04B 0.9800 . ?
C04 H04C 0.9800 . ?
F01 C01 1.33(2) . ?
F02 C01 1.368(19) . ?
F03 C01 1.350(19) . ?

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
O2 Fe1 O1 92.4(3) . . ?
O2 Fe1 N3 94.3(3) . . ?
O1 Fe1 N3 87.9(3) . . ?
O2 Fe1 N1 88.6(3) . . ?
O1 Fe1 N1 93.3(3) . . ?
N3 Fe1 N1 176.8(3) . . ?
O2 Fe1 N2 89.5(3) . . ?
O1 Fe1 N2 175.5(3) . . ?
N3 Fe1 N2 96.0(3) . . ?
N1 Fe1 N2 82.7(3) . . ?
O2 Fe1 N4 175.8(3) . . ?
O1 Fe1 N4 90.1(3) . . ?
N3 Fe1 N4 82.5(3) . . ?
N1 Fe1 N4 94.6(3) . . ?
N2 Fe1 N4 88.2(3) . . ?
C31 O2 Fe1 125.4(6) . . ?
C48 N4 C49 118.9(8) . . ?
C48 N4 Fe1 127.8(7) . . ?
C49 N4 Fe1 113.3(6) . . ?
C11 O1 Fe1 126.5(6) . . ?
O01 S01 O03 118.1(10) . . ?
O01 S01 O02 116.1(10) . . ?
O03 S01 O02 105.6(10) . . ?
O01 S01 C01 110.7(8) . . ?
O03 S01 C01 103.9(10) . . ?
O02 S01 C01 100.3(9) . . ?
C37 N3 C41 120.7(8) . . ?
C37 N3 Fe1 125.5(6) . . ?
C41 N3 Fe1 113.8(6) . . ?
C28 N2 C29 117.9(7) . . ?
C28 N2 Fe1 128.9(6) . . ?
C29 N2 Fe1 113.1(6) . . ?
C17 N1 C21 120.0(8) . . ?
C17 N1 Fe1 125.8(6) . . ?
C21 N1 Fe1 114.1(6) . . ?
C35 C36 C31 120.8(8) . . ?
C35 C36 C37 117.0(9) . . ?
C31 C36 C37 122.2(8) . . ?
C15 C16 C11 120.4(8) . . ?
C15 C16 C17 116.6(8) . . ?
C11 C16 C17 123.0(8) . . ?
N2 C29 C25 123.5(8) . . ?
N2 C29 C21 117.0(7) . . ?
C25 C29 C21 119.5(8) . . ?
C44 C45 C46 124.3(9) . . ?
C44 C45 C49 118.0(9) . . ?
C46 C45 C49 117.7(10) . . ?
C27 C26 C25 118.4(8) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C22 C21 N1 127.9(9) . . ?
C22 C21 C29 119.2(8) . . ?
N1 C21 C29 112.8(8) . . ?
C42 C41 N3 128.0(8) . . ?
C42 C41 C49 118.7(8) . . ?
N3 C41 C49 113.4(8) . . ?
C41 C42 C43 120.9(9) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C24 C25 C29 119.0(9) . . ?
C24 C25 C26 124.9(8) . . ?
C29 C25 C26 116.0(9) . . ?
C33 C32 C31 121.5(10) . . ?
C33 C32 H32 119.3 . . ?
C31 C32 H32 119.3 . . ?
C34 C35 C36 121.4(10) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C23 C24 C25 120.6(9) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
N3 C37 C36 126.2(9) . . ?
N3 C37 H37 116.9 . . ?
C36 C37 H37 116.9 . . ?
C46 C47 C48 119.1(9) . . ?
C46 C47 H47 120.4 . . ?
C48 C47 H47 120.4 . . ?
N1 C17 C16 125.4(9) . . ?
N1 C17 H17 117.3 . . ?
C16 C17 H17 117.3 . . ?
N4 C49 C41 116.9(8) . . ?
N4 C49 C45 122.3(8) . . ?
C41 C49 C45 120.8(9) . . ?
N4 C48 C47 122.5(10) . . ?
N4 C48 H48 118.7 . . ?
C47 C48 H48 118.7 . . ?
O1 C11 C16 125.5(7) . . ?
O1 C11 C12 117.6(9) . . ?
C16 C11 C12 116.9(9) . . ?
O2 C31 C36 126.1(8) . . ?
O2 C31 C32 117.5(9) . . ?
C36 C31 C32 116.3(9) . . ?
C14 C15 C16 121.9(9) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C43 C44 C45 121.2(9) . . ?
C43 C44 H44 119.4 . . ?
C45 C44 H44 119.4 . . ?
C34 C33 C32 120.7(9) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
N2 C28 C27 121.5(9) . . ?
N2 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C44 C43 C42 120.4(10) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C15 C14 C13 118.3(8) . . ?
C15 C14 I1 121.1(7) . . ?
C13 C14 I1 120.6(6) . . ?
C47 C46 C45 119.5(9) . . ?
C47 C46 H46 120.3 . . ?
C45 C46 H46 120.3 . . ?
C21 C22 C23 120.7(11) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C13 C12 C11 122.4(10) . . ?
C13 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
C26 C27 C28 122.6(10) . . ?
C26 C27 H27 118.7 . . ?
C28 C27 H27 118.7 . . ?
C12 C13 C14 120.1(8) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
O04 C02 C04 125.1(12) . . ?
O04 C02 C03 118.8(12) . . ?
C04 C02 C03 116.0(11) . . ?
C35 C34 C33 119.3(9) . . ?
C35 C34 I2 120.2(7) . . ?
C33 C34 I2 120.4(7) . . ?
C24 C23 C22 120.9(11) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C02 C03 H03A 109.5 . . ?
C02 C03 H03B 109.5 . . ?
H03A C03 H03B 109.5 . . ?
C02 C03 H03C 109.5 . . ?
H03A C03 H03C 109.5 . . ?
H03B C03 H03C 109.5 . . ?
C02 C04 H04A 109.5 . . ?
C02 C04 H04B 109.5 . . ?
H04A C04 H04B 109.5 . . ?
C02 C04 H04C 109.5 . . ?
H04A C04 H04C 109.5 . . ?
H04B C04 H04C 109.5 . . ?
F01 C01 F02 106(2) . . ?
F01 C01 S01 114(2) . . ?
F02 C01 S01 113(2) . . ?
F01 C01 F03 109(2) . . ?
F02 C01 F03 107(2) . . ?
S01 C01 F03 108(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C28 N2 C29 C25 1.3(13) . . . . ?
Fe1 N2 C29 C25 -175.4(7) . . . . ?
C28 N2 C29 C21 -177.8(8) . . . . ?
Fe1 N2 C29 C21 5.5(10) . . . . ?
C17 N1 C21 C22 -7.1(16) . . . . ?
Fe1 N1 C21 C22 174.8(10) . . . . ?
C17 N1 C21 C29 175.5(8) . . . . ?
Fe1 N1 C21 C29 -2.7(10) . . . . ?
N2 C29 C21 C22 -179.6(9) . . . . ?
C25 C29 C21 C22 1.3(14) . . . . ?
N2 C29 C21 N1 -1.9(12) . . . . ?
C25 C29 C21 N1 179.0(8) . . . . ?
C37 N3 C41 C42 2.6(12) . . . . ?
Fe1 N3 C41 C42 -176.1(7) . . . . ?
C37 N3 C41 C49 -178.0(7) . . . . ?
Fe1 N3 C41 C49 3.3(8) . . . . ?
N3 C41 C42 C43 179.2(8) . . . . ?
C49 C41 C42 C43 -0.2(12) . . . . ?
N2 C29 C25 C24 -179.5(9) . . . . ?
C21 C29 C25 C24 -0.4(14) . . . . ?
N2 C29 C25 C26 0.1(13) . . . . ?
C21 C29 C25 C26 179.1(8) . . . . ?
C27 C26 C25 C24 176.7(10) . . . . ?
C27 C26 C25 C29 -2.8(14) . . . . ?
C31 C36 C35 C34 -1.9(13) . . . . ?
C37 C36 C35 C34 179.7(8) . . . . ?
C29 C25 C24 C23 -0.1(17) . . . . ?
C26 C25 C24 C23 -179.6(12) . . . . ?
C41 N3 C37 C36 177.0(7) . . . . ?
Fe1 N3 C37 C36 -4.5(11) . . . . ?
C35 C36 C37 N3 -178.0(8) . . . . ?
C31 C36 C37 N3 3.6(13) . . . . ?
C21 N1 C17 C16 173.5(8) . . . . ?
Fe1 N1 C17 C16 -8.6(13) . . . . ?
C15 C16 C17 N1 -173.7(9) . . . . ?
C11 C16 C17 N1 2.5(15) . . . . ?
C48 N4 C49 C41 178.6(7) . . . . ?
Fe1 N4 C49 C41 -1.3(9) . . . . ?
C48 N4 C49 C45 -1.5(11) . . . . ?
Fe1 N4 C49 C45 178.6(6) . . . . ?
C42 C41 C49 N4 178.2(7) . . . . ?
N3 C41 C49 N4 -1.3(10) . . . . ?
C42 C41 C49 C45 -1.7(11) . . . . ?
N3 C41 C49 C45 178.8(7) . . . . ?
C44 C45 C49 N4 -177.8(7) . . . . ?
C46 C45 C49 N4 0.5(12) . . . . ?
C44 C45 C49 C41 2.1(12) . . . . ?
C46 C45 C49 C41 -179.5(7) . . . . ?
C49 N4 C48 C47 2.1(12) . . . . ?
Fe1 N4 C48 C47 -178.0(6) . . . . ?
C46 C47 C48 N4 -1.7(13) . . . . ?
Fe1 O1 C11 C16 0.7(13) . . . . ?
Fe1 O1 C11 C12 178.5(6) . . . . ?
C15 C16 C11 O1 177.9(9) . . . . ?
C17 C16 C11 O1 1.8(15) . . . . ?
C15 C16 C11 C12 0.1(14) . . . . ?
C17 C16 C11 C12 -176.0(9) . . . . ?
Fe1 O2 C31 C36 -5.6(11) . . . . ?
Fe1 O2 C31 C32 175.5(5) . . . . ?
C35 C36 C31 O2 -176.5(8) . . . . ?
C37 C36 C31 O2 1.9(13) . . . . ?
C35 C36 C31 C32 2.5(12) . . . . ?
C37 C36 C31 C32 -179.2(7) . . . . ?
C33 C32 C31 O2 177.0(8) . . . . ?
C33 C32 C31 C36 -2.0(12) . . . . ?
C11 C16 C15 C14 -1.5(15) . . . . ?
C17 C16 C15 C14 174.9(9) . . . . ?
C46 C45 C44 C43 -178.8(9) . . . . ?
C49 C45 C44 C43 -0.6(13) . . . . ?
C31 C32 C33 C34 0.8(13) . . . . ?
C29 N2 C28 C27 0.0(13) . . . . ?
Fe1 N2 C28 C27 176.1(7) . . . . ?
C45 C44 C43 C42 -1.3(14) . . . . ?
C41 C42 C43 C44 1.7(13) . . . . ?
C16 C15 C14 C13 2.0(15) . . . . ?
C16 C15 C14 I1 -176.0(7) . . . . ?
C48 C47 C46 C45 0.7(13) . . . . ?
C44 C45 C46 C47 178.1(8) . . . . ?
C49 C45 C46 C47 -0.1(12) . . . . ?
N1 C21 C22 C23 -179.0(11) . . . . ?
C29 C21 C22 C23 -1.7(18) . . . . ?
O1 C11 C12 C13 -177.3(9) . . . . ?
C16 C11 C12 C13 0.6(15) . . . . ?
C25 C26 C27 C28 4.2(15) . . . . ?
N2 C28 C27 C26 -2.9(15) . . . . ?
C11 C12 C13 C14 0.0(16) . . . . ?
C15 C14 C13 C12 -1.3(15) . . . . ?
I1 C14 C13 C12 176.8(8) . . . . ?
C36 C35 C34 C33 0.6(13) . . . . ?
C36 C35 C34 I2 178.2(6) . . . . ?
C32 C33 C34 C35 -0.1(13) . . . . ?
C32 C33 C34 I2 -177.7(6) . . . . ?
C25 C24 C23 C22 0(2) . . . . ?
C21 C22 C23 C24 1(2) . . . . ?
O01 S01 C01 F01 52.5(14) . . . . ?
O03 S01 C01 F01 -179.7(14) . . . . ?
O02 S01 C01 F01 -70.7(14) . . . . ?
O01 S01 C01 F02 173.2(12) . . . . ?
O03 S01 C01 F02 -59.0(15) . . . . ?
O02 S01 C01 F02 50.0(14) . . . . ?
O01 S01 C01 F03 -68.7(13) . . . . ?
O03 S01 C01 F03 59.1(15) . . . . ?
O02 S01 C01 F03 168.1(13) . . . . ?

_refine_diff_density_max         2.189
_refine_diff_density_min         -2.701
_refine_diff_density_rms         0.217

_shelxl_version_number           2013-2


# start Validation Reply Form
_vrf_CRYSS02_wp113-lt            
;
PROBLEM: The value of _exptl_crystal_size_max is > 1.0
RESPONSE: The crystals are fragile and their small fragments don't diffract nicely.
;
_vrf_PLAT431_wp113-lt            
;
PROBLEM: Short Inter HL..A Contact F02 .. O03 .. 2.56 Ang.
RESPONSE: The atomic coordinates of the OTf anion are not precisely defined by the experimental data due to significant thermal motion.
;
# end Validation Reply Form
####################################################################### 
# 
# 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_wp113-rt
_database_code_depnum_ccdc_archive 'CCDC 1519947'
_audit_update_record             
;
2016-11-30 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H20 Fe I2 N4 O2, C F3 O3 S, C3 H6 O'
_chemical_formula_sum            'C36 H26 F3 Fe I2 N4 O6 S'
_chemical_formula_weight         1009.32

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'
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'
F F 0.0727 0.0534 '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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   10.3585(6)
_cell_length_b                   12.9759(6)
_cell_length_c                   14.1074(3)
_cell_angle_alpha                78.558(6)
_cell_angle_beta                 76.606(6)
_cell_angle_gamma                86.265(4)
_cell_volume                     1807.59(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    23274
_cell_measurement_theta_min      6.57
_cell_measurement_theta_max      71.97

_exptl_crystal_description       rod
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_F_000             986
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.328
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    17.884
_shelx_estimated_absorpt_T_min   0.016
_shelx_estimated_absorpt_T_max   0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.134862
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a
_diffrn_source                   'Rigaku MM007 rotating anode'
_diffrn_measurement_device_type  'Rigaku Spider'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            25841
_diffrn_reflns_av_unetI/netI     0.0779
_diffrn_reflns_av_R_equivalents  0.0948
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.569
_diffrn_reflns_theta_max         72.045
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             6761
_reflns_number_gt                4448
_reflns_threshold_expression     'I > 2σ(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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'OLEX (Dolomanov, 2003) and SXGRAPH in WinGX v2013.1'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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/[σ²(Fo²)+(0.1523P)²+3.6056P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6761
_refine_ls_number_parameters     480
_refine_ls_number_restraints     181
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0920
_refine_ls_wR_factor_ref         0.3028
_refine_ls_wR_factor_gt          0.2474
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.177
_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
I1 I 1.33196(8) 0.05651(7) 0.06841(5) 0.0949(4) Uani 1 1 d . . . . .
I2 I 1.19475(10) 0.39311(8) 0.91325(6) 0.1039(4) Uani 1 1 d . . . . .
Fe1 Fe 0.87791(13) 0.24381(10) 0.51840(9) 0.0544(4) Uani 1 1 d . . . . .
O2 O 0.9866(6) 0.1901(6) 0.6132(5) 0.0713(17) Uani 1 1 d . U . . .
N4 N 0.7428(7) 0.3260(6) 0.4367(5) 0.0545(16) Uani 1 1 d . . . . .
O1 O 1.0259(7) 0.2825(6) 0.4062(5) 0.0698(18) Uani 1 1 d . . . . .
S01 S 0.6559(7) 0.4557(7) 0.8800(5) 0.178(2) Uani 1 1 d D U . . .
N3 N 0.8620(7) 0.3892(6) 0.5622(5) 0.0586(18) Uani 1 1 d . . . . .
N2 N 0.7082(7) 0.1779(6) 0.6218(5) 0.0553(17) Uani 1 1 d . . . . .
N1 N 0.8638(7) 0.1034(6) 0.4724(5) 0.0548(17) Uani 1 1 d . . . . .
O01 O 0.6677(12) 0.4426(10) 0.7936(7) 0.149(4) Uani 1 1 d D U . . .
C36 C 0.9953(9) 0.3407(7) 0.6866(7) 0.060(2) Uani 1 1 d . . . . .
C16 C 1.0574(8) 0.1271(7) 0.3346(7) 0.057(2) Uani 1 1 d . . . . .
C29 C 0.6694(8) 0.0862(7) 0.6042(6) 0.055(2) Uani 1 1 d . . . . .
C45 C 0.6407(9) 0.4955(9) 0.3905(7) 0.071(3) Uani 1 1 d . U . . .
O04 O 0.7826(9) 0.1123(9) 0.2134(8) 0.121(4) Uani 1 1 d . . . . .
C26 C 0.4780(9) 0.0839(8) 0.7390(7) 0.068(2) Uani 1 1 d . U . . .
H26 H 0.3994 0.0540 0.7779 0.082 Uiso 1 1 calc R U . . .
C21 C 0.7518(8) 0.0427(7) 0.5266(7) 0.056(2) Uani 1 1 d . . . . .
C41 C 0.7863(8) 0.4661(7) 0.5117(6) 0.057(2) Uani 1 1 d . . . . .
C42 C 0.7695(10) 0.5710(8) 0.5171(8) 0.069(2) Uani 1 1 d . . . . .
H42 H 0.8113 0.5979 0.5584 0.083 Uiso 1 1 calc R U . . .
C25 C 0.5529(9) 0.0356(8) 0.6643(7) 0.064(2) Uani 1 1 d . U . . .
C32 C 1.0981(10) 0.1767(9) 0.7430(8) 0.074(3) Uani 1 1 d . . . . .
H32 H 1.1148 0.1058 0.7414 0.089 Uiso 1 1 calc R U . . .
C35 C 1.0422(11) 0.3880(10) 0.7551(8) 0.077(3) Uani 1 1 d . U . . .
H35 H 1.0231 0.4583 0.7590 0.092 Uiso 1 1 calc R U . . .
C24 C 0.5224(12) -0.0612(10) 0.6415(10) 0.095(3) Uani 1 1 d . U . . .
H24 H 0.4466 -0.0969 0.6786 0.114 Uiso 1 1 calc R U . . .
C37 C 0.9178(9) 0.4113(9) 0.6277(7) 0.066(2) Uani 1 1 d . . . . .
H37 H 0.9071 0.4801 0.6385 0.079 Uiso 1 1 calc R U . . .
C47 C 0.6018(12) 0.3521(12) 0.3208(8) 0.089(4) Uani 1 1 d . . . . .
H47 H 0.5637 0.3242 0.2780 0.107 Uiso 1 1 calc R U . . .
C17 C 0.9483(8) 0.0690(7) 0.4004(6) 0.0536(19) Uani 1 1 d . . . . .
H17 H 0.9367 0.0015 0.3912 0.064 Uiso 1 1 calc R U . . .
C49 C 0.7200(8) 0.4279(7) 0.4454(6) 0.059(2) Uani 1 1 d . . . . .
C48 C 0.6842(10) 0.2881(9) 0.3762(7) 0.072(3) Uani 1 1 d . . . . .
H48 H 0.6982 0.2179 0.3704 0.086 Uiso 1 1 calc R U . . .
C11 C 1.0879(9) 0.2304(9) 0.3403(7) 0.066(3) Uani 1 1 d . . . . .
C31 C 1.0228(9) 0.2368(7) 0.6781(7) 0.059(2) Uani 1 1 d . U . . .
C15 C 1.1303(9) 0.0772(9) 0.2577(7) 0.066(2) Uani 1 1 d . . . . .
H15 H 1.1098 0.0091 0.2557 0.079 Uiso 1 1 calc R U . . .
C44 C 0.6267(11) 0.6030(10) 0.4015(9) 0.087(3) Uani 1 1 d . U . . .
H44 H 0.5734 0.6494 0.3673 0.105 Uiso 1 1 calc R U . . .
C33 C 1.1466(11) 0.2207(11) 0.8079(7) 0.080(3) Uani 1 1 d . U . . .
H33 H 1.1995 0.1802 0.8468 0.096 Uiso 1 1 calc R U . . .
C28 C 0.6354(10) 0.2190(9) 0.6941(7) 0.073(3) Uani 1 1 d . . . . .
H28 H 0.6618 0.2815 0.7061 0.087 Uiso 1 1 calc R U . . .
C43 C 0.6922(12) 0.6371(9) 0.4627(10) 0.088(4) Uani 1 1 d . . . . .
H43 H 0.6843 0.7077 0.4678 0.106 Uiso 1 1 calc R U . . .
C14 C 1.2303(11) 0.1278(10) 0.1864(7) 0.075(3) Uani 1 1 d . . . . .
C46 C 0.5774(11) 0.4566(11) 0.3300(8) 0.086(4) Uani 1 1 d . . . . .
H46 H 0.5201 0.4989 0.2962 0.103 Uiso 1 1 calc R U . . .
C22 C 0.7169(12) -0.0496(10) 0.5087(10) 0.095(3) Uani 1 1 d . U . . .
H22 H 0.7695 -0.0791 0.4575 0.114 Uiso 1 1 calc R U . . .
C12 C 1.1943(11) 0.2804(10) 0.2629(8) 0.081(3) Uani 1 1 d . . . . .
H12 H 1.2163 0.3486 0.2634 0.098 Uiso 1 1 calc R U . . .
C27 C 0.5178(10) 0.1719(9) 0.7548(8) 0.072(2) Uani 1 1 d . U . . .
H27 H 0.4686 0.2031 0.8061 0.086 Uiso 1 1 calc R U . . .
C13 C 1.2638(10) 0.2317(10) 0.1891(8) 0.076(3) Uani 1 1 d . . . . .
H13 H 1.3326 0.2660 0.1409 0.091 Uiso 1 1 calc R U . . .
C02 C 0.8563(12) 0.1609(12) 0.1427(9) 0.090(4) Uani 1 1 d . . . . .
C34 C 1.1178(10) 0.3257(10) 0.8165(7) 0.071(3) Uani 1 1 d . U . . .
C23 C 0.6007(12) -0.1014(11) 0.5679(11) 0.103(3) Uani 1 1 d . U . . .
H23 H 0.5787 -0.1648 0.5550 0.124 Uiso 1 1 calc R U . . .
C03 C 0.915(2) 0.1051(19) 0.0615(13) 0.149(7) Uani 1 1 d . . . . .
H03A H 1.0082 0.1181 0.0405 0.224 Uiso 1 1 calc R U . . .
H03B H 0.8732 0.1298 0.0067 0.224 Uiso 1 1 calc R U . . .
H03C H 0.9010 0.0310 0.0840 0.224 Uiso 1 1 calc R U . . .
C04 C 0.8962(17) 0.2695(13) 0.1352(13) 0.121(5) Uani 1 1 d . . . . .
H04A H 0.9025 0.2802 0.1994 0.181 Uiso 1 1 calc R U . . .
H04B H 0.8312 0.3177 0.1115 0.181 Uiso 1 1 calc R U . . .
H04C H 0.9809 0.2816 0.0898 0.181 Uiso 1 1 calc R U . . .
F01 F 0.6974(16) 0.2674(10) 0.9387(12) 0.263(5) Uani 1 1 d D U . . .
F02 F 0.6084(17) 0.3379(13) 1.0443(8) 0.262(5) Uani 1 1 d D U . . .
O02 O 0.7622(13) 0.4822(13) 0.8971(11) 0.222(6) Uani 1 1 d D U . . .
O03 O 0.5583(14) 0.5169(12) 0.9076(12) 0.257(7) Uani 1 1 d D U . . .
F03 F 0.5123(14) 0.3032(13) 0.9539(12) 0.268(5) Uani 1 1 d D U . . .
C01 C 0.6204(13) 0.346(3) 0.9508(18) 0.220(5) Uani 1 1 d D U . . .


_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
I1 C14 2.099(12) . ?
I2 C34 2.081(11) . ?
Fe1 O1 1.941(6) . ?
Fe1 O2 1.942(7) . ?
Fe1 N1 2.076(7) . ?
Fe1 N3 2.084(8) . ?
Fe1 N2 2.113(6) . ?
Fe1 N4 2.119(7) . ?
O2 C31 1.324(12) . ?
N4 C48 1.335(11) . ?
N4 C49 1.353(12) . ?
O1 C11 1.285(12) . ?
S01 O01 1.241(8) . ?
S01 O02 1.262(8) . ?
S01 O03 1.280(9) . ?
S01 C01 1.58(4) . ?
N3 C37 1.283(12) . ?
N3 C41 1.411(11) . ?
N2 C28 1.304(13) . ?
N2 C29 1.366(11) . ?
N1 C17 1.309(12) . ?
N1 C21 1.421(10) . ?
C36 C31 1.383(13) . ?
C36 C35 1.428(14) . ?
C36 C37 1.443(13) . ?
C16 C15 1.415(14) . ?
C16 C11 1.418(13) . ?
C16 C17 1.434(11) . ?
C29 C21 1.412(13) . ?
C29 C25 1.419(11) . ?
C45 C46 1.373(16) . ?
C45 C49 1.405(13) . ?
C45 C44 1.429(18) . ?
O04 C02 1.198(14) . ?
C26 C27 1.315(15) . ?
C26 C25 1.387(15) . ?
C26 H26 0.9300 . ?
C21 C22 1.359(14) . ?
C41 C42 1.376(13) . ?
C41 C49 1.456(13) . ?
C42 C43 1.380(16) . ?
C42 H42 0.9300 . ?
C25 C24 1.429(16) . ?
C32 C33 1.368(15) . ?
C32 C31 1.422(13) . ?
C32 H32 0.9300 . ?
C35 C34 1.404(15) . ?
C35 H35 0.9300 . ?
C24 C23 1.333(18) . ?
C24 H24 0.9300 . ?
C37 H37 0.9300 . ?
C47 C46 1.389(19) . ?
C47 C48 1.410(15) . ?
C47 H47 0.9300 . ?
C17 H17 0.9300 . ?
C48 H48 0.9300 . ?
C11 C12 1.443(12) . ?
C15 C14 1.364(14) . ?
C15 H15 0.9300 . ?
C44 C43 1.364(18) . ?
C44 H44 0.9300 . ?
C33 C34 1.399(17) . ?
C33 H33 0.9300 . ?
C28 C27 1.413(13) . ?
C28 H28 0.9300 . ?
C43 H43 0.9300 . ?
C14 C13 1.423(16) . ?
C46 H46 0.9300 . ?
C22 C23 1.419(14) . ?
C22 H22 0.9300 . ?
C12 C13 1.363(16) . ?
C12 H12 0.9300 . ?
C27 H27 0.9300 . ?
C13 H13 0.9300 . ?
C02 C03 1.47(2) . ?
C02 C04 1.47(2) . ?
C23 H23 0.9300 . ?
C03 H03A 0.9600 . ?
C03 H03B 0.9600 . ?
C03 H03C 0.9600 . ?
C04 H04A 0.9600 . ?
C04 H04B 0.9600 . ?
C04 H04C 0.9600 . ?
F01 C01 1.27(2) . ?
F02 C01 1.280(19) . ?
F03 C01 1.270(19) . ?

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 O2 95.5(3) . . ?
O1 Fe1 N1 89.6(3) . . ?
O2 Fe1 N1 97.1(3) . . ?
O1 Fe1 N3 95.0(3) . . ?
O2 Fe1 N3 90.1(3) . . ?
N1 Fe1 N3 171.1(3) . . ?
O1 Fe1 N2 167.2(3) . . ?
O2 Fe1 N2 90.1(3) . . ?
N1 Fe1 N2 78.4(3) . . ?
N3 Fe1 N2 96.5(3) . . ?
O1 Fe1 N4 91.0(3) . . ?
O2 Fe1 N4 167.2(3) . . ?
N1 Fe1 N4 94.0(3) . . ?
N3 Fe1 N4 78.4(3) . . ?
N2 Fe1 N4 85.8(3) . . ?
C31 O2 Fe1 129.6(6) . . ?
C48 N4 C49 118.5(8) . . ?
C48 N4 Fe1 126.5(7) . . ?
C49 N4 Fe1 114.9(5) . . ?
C11 O1 Fe1 130.7(6) . . ?
O01 S01 O02 113.4(8) . . ?
O01 S01 O03 113.1(8) . . ?
O02 S01 O03 112.0(8) . . ?
O01 S01 C01 107.3(8) . . ?
O02 S01 C01 105.4(8) . . ?
O03 S01 C01 104.7(8) . . ?
C37 N3 C41 120.7(9) . . ?
C37 N3 Fe1 124.5(7) . . ?
C41 N3 Fe1 114.8(6) . . ?
C28 N2 C29 118.9(7) . . ?
C28 N2 Fe1 126.8(7) . . ?
C29 N2 Fe1 114.2(6) . . ?
C17 N1 C21 120.1(8) . . ?
C17 N1 Fe1 125.3(6) . . ?
C21 N1 Fe1 114.6(6) . . ?
C31 C36 C35 122.4(9) . . ?
C31 C36 C37 123.8(9) . . ?
C35 C36 C37 113.8(9) . . ?
C15 C16 C11 120.8(8) . . ?
C15 C16 C17 115.4(8) . . ?
C11 C16 C17 123.7(9) . . ?
N2 C29 C21 117.4(7) . . ?
N2 C29 C25 120.7(9) . . ?
C21 C29 C25 121.9(8) . . ?
C46 C45 C49 119.7(11) . . ?
C46 C45 C44 122.2(11) . . ?
C49 C45 C44 118.1(10) . . ?
C27 C26 C25 120.2(8) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C22 C21 C29 118.6(8) . . ?
C22 C21 N1 126.2(9) . . ?
C29 C21 N1 115.2(8) . . ?
C42 C41 N3 128.1(9) . . ?
C42 C41 C49 117.2(9) . . ?
N3 C41 C49 114.7(8) . . ?
C41 C42 C43 121.5(11) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 H42 119.2 . . ?
C26 C25 C29 118.0(9) . . ?
C26 C25 C24 125.6(9) . . ?
C29 C25 C24 116.5(10) . . ?
C33 C32 C31 121.7(11) . . ?
C33 C32 H32 119.1 . . ?
C31 C32 H32 119.1 . . ?
C34 C35 C36 118.3(11) . . ?
C34 C35 H35 120.8 . . ?
C36 C35 H35 120.8 . . ?
C23 C24 C25 121.1(10) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 H24 119.4 . . ?
N3 C37 C36 126.9(10) . . ?
N3 C37 H37 116.6 . . ?
C36 C37 H37 116.6 . . ?
C46 C47 C48 120.0(10) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
N1 C17 C16 125.2(9) . . ?
N1 C17 H17 117.4 . . ?
C16 C17 H17 117.4 . . ?
N4 C49 C45 122.1(9) . . ?
N4 C49 C41 116.7(8) . . ?
C45 C49 C41 121.1(9) . . ?
N4 C48 C47 121.6(11) . . ?
N4 C48 H48 119.2 . . ?
C47 C48 H48 119.2 . . ?
O1 C11 C16 125.1(8) . . ?
O1 C11 C12 118.7(9) . . ?
C16 C11 C12 116.1(10) . . ?
O2 C31 C36 125.0(8) . . ?
O2 C31 C32 118.0(9) . . ?
C36 C31 C32 117.0(9) . . ?
C14 C15 C16 120.8(10) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C43 C44 C45 119.5(10) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C32 C33 C34 120.9(10) . . ?
C32 C33 H33 119.5 . . ?
C34 C33 H33 119.5 . . ?
N2 C28 C27 122.3(10) . . ?
N2 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
C44 C43 C42 122.5(12) . . ?
C44 C43 H43 118.7 . . ?
C42 C43 H43 118.7 . . ?
C15 C14 C13 120.2(10) . . ?
C15 C14 I1 120.7(9) . . ?
C13 C14 I1 119.0(7) . . ?
C45 C46 C47 117.9(10) . . ?
C45 C46 H46 121.1 . . ?
C47 C46 H46 121.1 . . ?
C21 C22 C23 120.4(11) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C13 C12 C11 122.7(11) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C26 C27 C28 120.0(10) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C12 C13 C14 119.4(9) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
O04 C02 C03 116.9(16) . . ?
O04 C02 C04 124.1(14) . . ?
C03 C02 C04 118.9(14) . . ?
C33 C34 C35 119.5(10) . . ?
C33 C34 I2 120.8(8) . . ?
C35 C34 I2 119.6(9) . . ?
C24 C23 C22 121.5(12) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C02 C03 H03A 109.5 . . ?
C02 C03 H03B 109.5 . . ?
H03A C03 H03B 109.5 . . ?
C02 C03 H03C 109.5 . . ?
H03A C03 H03C 109.5 . . ?
H03B C03 H03C 109.5 . . ?
C02 C04 H04A 109.5 . . ?
C02 C04 H04B 109.5 . . ?
H04A C04 H04B 109.5 . . ?
C02 C04 H04C 109.5 . . ?
H04A C04 H04C 109.5 . . ?
H04B C04 H04C 109.5 . . ?
F01 C01 F03 98(2) . . ?
F01 C01 F02 98(2) . . ?
F03 C01 F02 98(2) . . ?
F01 C01 S01 119.4(17) . . ?
F03 C01 S01 119.2(17) . . ?
F02 C01 S01 119.4(17) . . ?

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
C28 N2 C29 C21 -178.8(9) . . . . ?
Fe1 N2 C29 C21 5.4(10) . . . . ?
C28 N2 C29 C25 -0.9(13) . . . . ?
Fe1 N2 C29 C25 -176.7(6) . . . . ?
N2 C29 C21 C22 178.7(10) . . . . ?
C25 C29 C21 C22 0.8(15) . . . . ?
N2 C29 C21 N1 -2.9(12) . . . . ?
C25 C29 C21 N1 179.3(8) . . . . ?
C17 N1 C21 C22 -3.3(15) . . . . ?
Fe1 N1 C21 C22 177.1(10) . . . . ?
C17 N1 C21 C29 178.4(8) . . . . ?
Fe1 N1 C21 C29 -1.2(10) . . . . ?
C37 N3 C41 C42 5.5(13) . . . . ?
Fe1 N3 C41 C42 -172.8(8) . . . . ?
C37 N3 C41 C49 -175.3(7) . . . . ?
Fe1 N3 C41 C49 6.4(8) . . . . ?
N3 C41 C42 C43 179.8(9) . . . . ?
C49 C41 C42 C43 0.6(13) . . . . ?
C27 C26 C25 C29 -2.5(15) . . . . ?
C27 C26 C25 C24 178.2(11) . . . . ?
N2 C29 C25 C26 2.1(13) . . . . ?
C21 C29 C25 C26 179.9(9) . . . . ?
N2 C29 C25 C24 -178.5(10) . . . . ?
C21 C29 C25 C24 -0.8(14) . . . . ?
C31 C36 C35 C34 -0.6(14) . . . . ?
C37 C36 C35 C34 179.5(8) . . . . ?
C26 C25 C24 C23 179.8(13) . . . . ?
C29 C25 C24 C23 0.6(19) . . . . ?
C41 N3 C37 C36 178.5(8) . . . . ?
Fe1 N3 C37 C36 -3.2(12) . . . . ?
C31 C36 C37 N3 1.4(14) . . . . ?
C35 C36 C37 N3 -178.7(8) . . . . ?
C21 N1 C17 C16 173.8(8) . . . . ?
Fe1 N1 C17 C16 -6.7(12) . . . . ?
C15 C16 C17 N1 -175.6(8) . . . . ?
C11 C16 C17 N1 0.5(14) . . . . ?
C48 N4 C49 C45 -2.1(12) . . . . ?
Fe1 N4 C49 C45 175.3(6) . . . . ?
C48 N4 C49 C41 -179.7(8) . . . . ?
Fe1 N4 C49 C41 -2.4(9) . . . . ?
C46 C45 C49 N4 3.7(13) . . . . ?
C44 C45 C49 N4 -177.5(8) . . . . ?
C46 C45 C49 C41 -178.7(9) . . . . ?
C44 C45 C49 C41 0.0(13) . . . . ?
C42 C41 C49 N4 176.7(8) . . . . ?
N3 C41 C49 N4 -2.6(10) . . . . ?
C42 C41 C49 C45 -1.0(12) . . . . ?
N3 C41 C49 C45 179.7(7) . . . . ?
C49 N4 C48 C47 0.9(14) . . . . ?
Fe1 N4 C48 C47 -176.1(8) . . . . ?
C46 C47 C48 N4 -1.4(17) . . . . ?
Fe1 O1 C11 C16 1.1(15) . . . . ?
Fe1 O1 C11 C12 178.7(7) . . . . ?
C15 C16 C11 O1 178.7(9) . . . . ?
C17 C16 C11 O1 2.8(15) . . . . ?
C15 C16 C11 C12 1.1(14) . . . . ?
C17 C16 C11 C12 -174.9(9) . . . . ?
Fe1 O2 C31 C36 -4.6(13) . . . . ?
Fe1 O2 C31 C32 176.8(6) . . . . ?
C35 C36 C31 O2 -177.1(8) . . . . ?
C37 C36 C31 O2 2.8(14) . . . . ?
C35 C36 C31 C32 1.5(13) . . . . ?
C37 C36 C31 C32 -178.6(8) . . . . ?
C33 C32 C31 O2 175.8(9) . . . . ?
C33 C32 C31 C36 -3.0(14) . . . . ?
C11 C16 C15 C14 -1.0(14) . . . . ?
C17 C16 C15 C14 175.3(8) . . . . ?
C46 C45 C44 C43 -179.9(10) . . . . ?
C49 C45 C44 C43 1.3(15) . . . . ?
C31 C32 C33 C34 3.4(16) . . . . ?
C29 N2 C28 C27 0.1(15) . . . . ?
Fe1 N2 C28 C27 175.2(7) . . . . ?
C45 C44 C43 C42 -1.8(17) . . . . ?
C41 C42 C43 C44 0.8(17) . . . . ?
C16 C15 C14 C13 0.7(15) . . . . ?
C16 C15 C14 I1 -176.9(7) . . . . ?
C49 C45 C46 C47 -4.1(15) . . . . ?
C44 C45 C46 C47 177.3(10) . . . . ?
C48 C47 C46 C45 3.0(17) . . . . ?
C29 C21 C22 C23 -0.7(19) . . . . ?
N1 C21 C22 C23 -178.9(12) . . . . ?
O1 C11 C12 C13 -178.9(10) . . . . ?
C16 C11 C12 C13 -1.0(16) . . . . ?
C25 C26 C27 C28 1.7(16) . . . . ?
N2 C28 C27 C26 -0.4(17) . . . . ?
C11 C12 C13 C14 0.9(18) . . . . ?
C15 C14 C13 C12 -0.7(16) . . . . ?
I1 C14 C13 C12 177.0(9) . . . . ?
C32 C33 C34 C35 -2.4(15) . . . . ?
C32 C33 C34 I2 -178.9(7) . . . . ?
C36 C35 C34 C33 1.0(14) . . . . ?
C36 C35 C34 I2 177.5(7) . . . . ?
C25 C24 C23 C22 0(2) . . . . ?
C21 C22 C23 C24 0(2) . . . . ?
O01 S01 C01 F01 56.9(12) . . . . ?
O02 S01 C01 F01 -64.4(12) . . . . ?
O03 S01 C01 F01 177.4(12) . . . . ?
O01 S01 C01 F03 -63.2(12) . . . . ?
O02 S01 C01 F03 175.6(12) . . . . ?
O03 S01 C01 F03 57.3(13) . . . . ?
O01 S01 C01 F02 177.1(11) . . . . ?
O02 S01 C01 F02 55.9(12) . . . . ?
O03 S01 C01 F02 -62.4(12) . . . . ?

_refine_diff_density_max         0.842
_refine_diff_density_min         -1.758
_refine_diff_density_rms         0.174

_shelxl_version_number           2013-2


# start Validation Reply Form
_vrf_CRYSS02_wp113-rt            
;
PROBLEM: The value of _exptl_crystal_size_max is > 1.0
RESPONSE: The crystals are fragile and their small fragments don't diffract nicely.
;
_vrf_PLAT431_wp113-rt            
;
PROBLEM: Short Inter HL..A  Contact F02    ..  O03     ..       2.56 Ang.  
RESPONSE: The atomic coordinates of the OTf anion are not precisely defined by the experimental data due to significant thermal motion.
;
# end Validation Reply Form
