# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

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#                                CCDC 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_1@100K

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis(3-methoxy-2-oxido-benzylidene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 Fe N4 O4 S'
_chemical_formula_weight         525.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.0809(7)
_cell_length_b                   11.3904(4)
_cell_length_c                   23.6108(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.420(2)
_cell_angle_gamma                90
_cell_volume                     4896.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9964
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.13

_exptl_crystal_description       block
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             2200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.739
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.866
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker X8 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55450
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.003
_diffrn_reflns_theta_max         27.156
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10842
_reflns_number_gt                8585
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0281P)²+2.7306P] 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         10842
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0322
_refine_ls_wR_factor_ref         0.0764
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.71669(2) 0.23001(2) 0.89286(2) 0.01041(6) Uani 1 1 d . . . . .
Fe2 Fe 0.79703(2) 0.71144(2) 1.08676(2) 0.01126(6) Uani 1 1 d . . . . .
S1 S 0.57052(3) 0.42562(4) 0.71313(2) 0.01950(11) Uani 1 1 d . . . . .
S2 S 0.93775(3) 0.54406(5) 1.27545(2) 0.02271(12) Uani 1 1 d . . . . .
O1 O 0.80025(7) 0.31595(11) 0.88587(5) 0.0134(3) Uani 1 1 d . . . . .
O2 O 0.77127(7) 0.14467(10) 0.96322(5) 0.0125(3) Uani 1 1 d . . . . .
O3 O 0.71590(7) 0.61782(11) 1.09394(5) 0.0146(3) Uani 1 1 d . . . . .
O4 O 0.74117(7) 0.78877(11) 1.01384(5) 0.0131(3) Uani 1 1 d . . . . .
O5 O 0.87675(7) 0.50202(11) 0.87539(5) 0.0169(3) Uani 1 1 d . . . . .
O6 O 0.90667(7) 0.05319(11) 1.02246(5) 0.0157(3) Uani 1 1 d . . . . .
O7 O 0.60902(7) 0.87040(11) 0.94419(5) 0.0161(3) Uani 1 1 d . . . . .
N1 N 0.73921(8) 0.10204(13) 0.83773(6) 0.0129(3) Uani 1 1 d . . . . .
N2 N 0.62430(8) 0.11135(13) 0.88435(7) 0.0137(3) Uani 1 1 d . . . . .
H2 H 0.6366 0.0625 0.9212 0.016 Uiso 1 1 calc R U . . .
N3 N 0.67634(8) 0.32754(13) 0.95090(6) 0.0123(3) Uani 1 1 d . . . . .
N4 N 0.64936(8) 0.31556(14) 0.81846(7) 0.0156(3) Uani 1 1 d . . . . .
N5 N 0.76313(8) 0.84537(13) 1.13322(6) 0.0145(3) Uani 1 1 d . . . . .
N6 N 0.88789(8) 0.83699(13) 1.09835(7) 0.0145(3) Uani 1 1 d . . . . .
H6 H 0.8778 0.8822 1.0605 0.017 Uiso 1 1 calc R U . . .
N7 N 0.84677(8) 0.61920(13) 1.03264(6) 0.0130(3) Uani 1 1 d . . . . .
N8 N 0.86261(9) 0.63364(14) 1.16399(7) 0.0182(3) Uani 1 1 d . . . . .
C1 C 0.82648(10) 0.31814(16) 0.84002(7) 0.0119(4) Uani 1 1 d . . . . .
C2 C 0.86876(10) 0.41659(16) 0.83288(8) 0.0140(4) Uani 1 1 d . . . . .
C3 C 0.90062(10) 0.42067(17) 0.78762(8) 0.0177(4) Uani 1 1 d . . . . .
H3 H 0.9297 0.4865 0.7842 0.021 Uiso 1 1 calc R U . . .
C4 C 0.89050(11) 0.32885(17) 0.74673(8) 0.0195(4) Uani 1 1 d . . . . .
H4 H 0.9123 0.3325 0.7155 0.023 Uiso 1 1 calc R U . . .
C5 C 0.84913(11) 0.23364(17) 0.75186(8) 0.0176(4) Uani 1 1 d . . . . .
H5 H 0.8420 0.1718 0.7237 0.021 Uiso 1 1 calc R U . . .
C6 C 0.81690(10) 0.22582(16) 0.79833(8) 0.0139(4) Uani 1 1 d . . . . .
C7 C 0.77608(10) 0.11981(16) 0.80118(8) 0.0138(4) Uani 1 1 d . . . . .
H7 H 0.7767 0.0588 0.7739 0.017 Uiso 1 1 calc R U . . .
C8 C 0.69731(10) -0.00623(16) 0.83619(8) 0.0159(4) Uani 1 1 d . . . . .
H8A H 0.7199 -0.0541 0.8720 0.019 Uiso 1 1 calc R U . . .
H8B H 0.6963 -0.0532 0.8007 0.019 Uiso 1 1 calc R U . . .
C9 C 0.62011(10) 0.03035(17) 0.83416(8) 0.0167(4) Uani 1 1 d . . . . .
H9A H 0.5958 0.0701 0.7960 0.020 Uiso 1 1 calc R U . . .
H9B H 0.5908 -0.0398 0.8372 0.020 Uiso 1 1 calc R U . . .
C10 C 0.55175(10) 0.16622(17) 0.87799(8) 0.0176(4) Uani 1 1 d . . . . .
H10A H 0.5156 0.1033 0.8770 0.021 Uiso 1 1 calc R U . . .
H10B H 0.5356 0.2078 0.8394 0.021 Uiso 1 1 calc R U . . .
C11 C 0.55084(10) 0.25250(17) 0.92696(8) 0.0177(4) Uani 1 1 d . . . . .
H11A H 0.5668 0.2103 0.9653 0.021 Uiso 1 1 calc R U . . .
H11B H 0.4995 0.2780 0.9207 0.021 Uiso 1 1 calc R U . . .
C12 C 0.59862(10) 0.36229(16) 0.93213(8) 0.0162(4) Uani 1 1 d . . . . .
H12A H 0.5865 0.4029 0.8933 0.019 Uiso 1 1 calc R U . . .
H12B H 0.5890 0.4170 0.9615 0.019 Uiso 1 1 calc R U . . .
C13 C 0.71620(10) 0.35321(16) 1.00382(8) 0.0138(4) Uani 1 1 d . . . . .
H13 H 0.6969 0.4074 1.0259 0.017 Uiso 1 1 calc R U . . .
C14 C 0.78858(10) 0.30500(16) 1.03205(8) 0.0126(4) Uani 1 1 d . . . . .
C15 C 0.83155(10) 0.35486(16) 1.08561(8) 0.0151(4) Uani 1 1 d . . . . .
H15 H 0.8138 0.4214 1.1014 0.018 Uiso 1 1 calc R U . . .
C16 C 0.89910(10) 0.30823(17) 1.11541(8) 0.0167(4) Uani 1 1 d . . . . .
H16 H 0.9281 0.3430 1.1514 0.020 Uiso 1 1 calc R U . . .
C17 C 0.92488(10) 0.21007(17) 1.09271(8) 0.0161(4) Uani 1 1 d . . . . .
H17 H 0.9721 0.1793 1.1128 0.019 Uiso 1 1 calc R U . . .
C18 C 0.88248(10) 0.15698(16) 1.04130(8) 0.0136(4) Uani 1 1 d . . . . .
C19 C 0.81248(10) 0.20130(15) 1.01006(7) 0.0116(4) Uani 1 1 d . . . . .
C20 C 0.67741(10) 0.62728(16) 1.13150(7) 0.0132(4) Uani 1 1 d . . . . .
C21 C 0.63837(10) 0.52757(17) 1.14230(8) 0.0158(4) Uani 1 1 d . . . . .
C22 C 0.59164(10) 0.53594(18) 1.17718(8) 0.0188(4) Uani 1 1 d . . . . .
H22 H 0.5641 0.4694 1.1821 0.023 Uiso 1 1 calc R U . . .
C23 C 0.58482(11) 0.64143(18) 1.20512(8) 0.0199(4) Uani 1 1 d . . . . .
H23 H 0.5523 0.6467 1.2286 0.024 Uiso 1 1 calc R U . . .
C24 C 0.62488(10) 0.73721(17) 1.19865(8) 0.0178(4) Uani 1 1 d . . . . .
H24 H 0.6212 0.8080 1.2188 0.021 Uiso 1 1 calc R U . . .
C25 C 0.67181(10) 0.73231(16) 1.16233(8) 0.0138(4) Uani 1 1 d . . . . .
C26 C 0.71376(10) 0.83691(17) 1.15968(8) 0.0156(4) Uani 1 1 d . . . . .
H26 H 0.7038 0.9050 1.1792 0.019 Uiso 1 1 calc R U . . .
C27 C 0.80395(11) 0.95522(17) 1.13476(9) 0.0189(4) Uani 1 1 d . . . . .
H27A H 0.7991 1.0063 1.1673 0.023 Uiso 1 1 calc R U . . .
H27B H 0.7848 0.9981 1.0968 0.023 Uiso 1 1 calc R U . . .
C28 C 0.88385(10) 0.92156(17) 1.14489(8) 0.0178(4) Uani 1 1 d . . . . .
H28A H 0.9132 0.9923 1.1430 0.021 Uiso 1 1 calc R U . . .
H28B H 0.9041 0.8855 1.1846 0.021 Uiso 1 1 calc R U . . .
C29 C 0.96320(10) 0.78716(17) 1.11089(8) 0.0184(4) Uani 1 1 d . . . . .
H29A H 0.9760 0.7454 1.1494 0.022 Uiso 1 1 calc R U . . .
H29B H 0.9986 0.8523 1.1146 0.022 Uiso 1 1 calc R U . . .
C30 C 0.97091(10) 0.70250(17) 1.06306(8) 0.0185(4) Uani 1 1 d . . . . .
H30A H 1.0233 0.6804 1.0721 0.022 Uiso 1 1 calc R U . . .
H30B H 0.9568 0.7444 1.0246 0.022 Uiso 1 1 calc R U . . .
C31 C 0.92532(10) 0.59001(17) 1.05606(8) 0.0167(4) Uani 1 1 d . . . . .
H31A H 0.9393 0.5357 1.0285 0.020 Uiso 1 1 calc R U . . .
H31B H 0.9350 0.5505 1.0950 0.020 Uiso 1 1 calc R U . . .
C32 C 0.81242(10) 0.59028(15) 0.97853(8) 0.0136(4) Uani 1 1 d . . . . .
H32 H 0.8361 0.5370 0.9593 0.016 Uiso 1 1 calc R U . . .
C33 C 0.74046(10) 0.63305(16) 0.94507(8) 0.0131(4) Uani 1 1 d . . . . .
C34 C 0.70546(11) 0.58124(16) 0.88972(8) 0.0165(4) Uani 1 1 d . . . . .
H34 H 0.7279 0.5166 0.8766 0.020 Uiso 1 1 calc R U . . .
C35 C 0.63911(11) 0.62294(17) 0.85435(8) 0.0180(4) Uani 1 1 d . . . . .
H35 H 0.6157 0.5869 0.8172 0.022 Uiso 1 1 calc R U . . .
C36 C 0.60624(10) 0.71900(16) 0.87355(8) 0.0166(4) Uani 1 1 d . . . . .
H36 H 0.5600 0.7473 0.8496 0.020 Uiso 1 1 calc R U . . .
C37 C 0.64056(10) 0.77255(16) 0.92687(8) 0.0131(4) Uani 1 1 d . . . . .
C38 C 0.70915(10) 0.73245(15) 0.96432(7) 0.0114(4) Uani 1 1 d . . . . .
C39 C 0.89878(12) 0.61733(18) 0.86253(9) 0.0254(5) Uani 1 1 d . . . . .
H39A H 0.9438 0.6106 0.8501 0.031 Uiso 1 1 calc R U . . .
H39B H 0.9108 0.6653 0.8991 0.031 Uiso 1 1 calc R U . . .
C40 C 0.84040(14) 0.67902(19) 0.81453(10) 0.0350(6) Uani 1 1 d . . . . .
H40A H 0.8305 0.6346 0.7774 0.052 Uiso 1 1 calc R U . . .
H40B H 0.8573 0.7581 0.8088 0.052 Uiso 1 1 calc R U . . .
H40C H 0.7953 0.6845 0.8261 0.052 Uiso 1 1 calc R U . . .
C41 C 0.91312(10) 0.05681(17) 0.96260(8) 0.0169(4) Uani 1 1 d . . . . .
H41A H 0.9647 0.0724 0.9642 0.020 Uiso 1 1 calc R U . . .
H41B H 0.8821 0.1207 0.9397 0.020 Uiso 1 1 calc R U . . .
C42 C 0.88882(12) -0.05898(18) 0.93289(9) 0.0254(5) Uani 1 1 d . . . . .
H42A H 0.9232 -0.1205 0.9530 0.038 Uiso 1 1 calc R U . . .
H42B H 0.8878 -0.0544 0.8912 0.038 Uiso 1 1 calc R U . . .
H42C H 0.8396 -0.0777 0.9351 0.038 Uiso 1 1 calc R U . . .
C43 C 0.58424(11) 0.84952(17) 0.99566(8) 0.0187(4) Uani 1 1 d . . . . .
H43A H 0.6128 0.7848 1.0198 0.022 Uiso 1 1 calc R U . . .
H43B H 0.5317 0.8272 0.9830 0.022 Uiso 1 1 calc R U . . .
C44 C 0.59517(11) 0.96054(18) 1.03145(9) 0.0220(4) Uani 1 1 d . . . . .
H44A H 0.6472 0.9826 1.0432 0.033 Uiso 1 1 calc R U . . .
H44B H 0.5797 0.9480 1.0670 0.033 Uiso 1 1 calc R U . . .
H44C H 0.5657 1.0236 1.0075 0.033 Uiso 1 1 calc R U . . .
C47 C 0.61732(10) 0.36064(15) 0.77409(8) 0.0123(4) Uani 1 1 d . . . . .
C48 C 0.89359(10) 0.59717(16) 1.21076(8) 0.0141(4) Uani 1 1 d . . . . .
O8 O 0.65083(8) 0.42635(11) 1.11586(6) 0.0197(3) Uani 1 1 d . . . . .
C45 C 0.62884(12) 0.31829(17) 1.13742(9) 0.0242(5) Uani 1 1 d . . . . .
H45A H 0.5748 0.3094 1.1226 0.029 Uiso 1 1 calc R U . . .
H45B H 0.6440 0.3183 1.1814 0.029 Uiso 1 1 calc R U . . .
C46 C 0.66552(14) 0.21919(18) 1.11524(10) 0.0305(5) Uani 1 1 d . . . . .
H46A H 0.6486 0.2181 1.0718 0.046 Uiso 1 1 calc R U . . .
H46B H 0.6529 0.1446 1.1304 0.046 Uiso 1 1 calc R U . . .
H46C H 0.7189 0.2303 1.1291 0.046 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
Fe1 O1 1.9197(12) . ?
Fe1 O2 1.9373(12) . ?
Fe1 N4 2.0819(15) . ?
Fe1 N3 2.0823(15) . ?
Fe1 N1 2.0830(15) . ?
Fe1 N2 2.1824(15) . ?
Fe2 O3 1.9286(13) . ?
Fe2 O4 1.9434(12) . ?
Fe2 N8 2.0761(16) . ?
Fe2 N7 2.0889(15) . ?
Fe2 N5 2.0914(15) . ?
Fe2 N6 2.2003(15) . ?
S1 C47 1.6272(19) . ?
S2 C48 1.6242(19) . ?
O1 C1 1.322(2) . ?
O2 C19 1.318(2) . ?
O3 C20 1.314(2) . ?
O4 C38 1.313(2) . ?
O5 C2 1.373(2) . ?
O5 C39 1.439(2) . ?
O6 C18 1.390(2) . ?
O6 C41 1.456(2) . ?
O7 C37 1.385(2) . ?
O7 C43 1.449(2) . ?
N1 C7 1.282(2) . ?
N1 C8 1.464(2) . ?
N2 C10 1.485(2) . ?
N2 C9 1.485(2) . ?
N3 C13 1.287(2) . ?
N3 C12 1.469(2) . ?
N4 C47 1.163(2) . ?
N5 C26 1.280(2) . ?
N5 C27 1.468(2) . ?
N6 C28 1.480(2) . ?
N6 C29 1.490(2) . ?
N7 C32 1.292(2) . ?
N7 C31 1.472(2) . ?
N8 C48 1.162(2) . ?
C1 C6 1.414(3) . ?
C1 C2 1.421(3) . ?
C2 C3 1.379(2) . ?
C3 C4 1.397(3) . ?
C4 C5 1.368(3) . ?
C5 C6 1.412(2) . ?
C6 C7 1.449(3) . ?
C8 C9 1.518(3) . ?
C10 C11 1.522(3) . ?
C11 C12 1.531(3) . ?
C13 C14 1.450(3) . ?
C14 C15 1.405(2) . ?
C14 C19 1.420(2) . ?
C15 C16 1.377(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.380(3) . ?
C18 C19 1.412(2) . ?
C20 C25 1.421(3) . ?
C20 C21 1.423(3) . ?
C21 O8 1.366(2) . ?
C21 C22 1.386(2) . ?
C22 C23 1.395(3) . ?
C23 C24 1.367(3) . ?
C24 C25 1.414(2) . ?
C25 C26 1.447(3) . ?
C27 C28 1.520(3) . ?
C29 C30 1.525(3) . ?
C30 C31 1.530(3) . ?
C32 C33 1.448(3) . ?
C33 C34 1.407(3) . ?
C33 C38 1.417(2) . ?
C34 C35 1.376(3) . ?
C35 C36 1.402(3) . ?
C36 C37 1.376(3) . ?
C37 C38 1.418(2) . ?
C39 C40 1.504(3) . ?
C41 C42 1.501(3) . ?
C43 C44 1.500(3) . ?
O8 C45 1.442(2) . ?
C45 C46 1.503(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Fe1 O2 94.73(5) . . ?
O1 Fe1 N4 90.42(6) . . ?
O2 Fe1 N4 174.78(6) . . ?
O1 Fe1 N3 105.35(6) . . ?
O2 Fe1 N3 85.02(5) . . ?
N4 Fe1 N3 92.82(6) . . ?
O1 Fe1 N1 88.34(6) . . ?
O2 Fe1 N1 91.51(5) . . ?
N4 Fe1 N1 89.48(6) . . ?
N3 Fe1 N1 166.09(6) . . ?
O1 Fe1 N2 167.61(5) . . ?
O2 Fe1 N2 88.87(5) . . ?
N4 Fe1 N2 86.26(6) . . ?
N3 Fe1 N2 86.75(6) . . ?
N1 Fe1 N2 79.70(6) . . ?
O3 Fe2 O4 94.97(5) . . ?
O3 Fe2 N8 88.59(6) . . ?
O4 Fe2 N8 176.40(6) . . ?
O3 Fe2 N7 107.42(6) . . ?
O4 Fe2 N7 85.14(5) . . ?
N8 Fe2 N7 93.31(6) . . ?
O3 Fe2 N5 88.55(6) . . ?
O4 Fe2 N5 87.73(5) . . ?
N8 Fe2 N5 92.89(6) . . ?
N7 Fe2 N5 162.99(6) . . ?
O3 Fe2 N6 166.34(5) . . ?
O4 Fe2 N6 91.06(6) . . ?
N8 Fe2 N6 85.57(6) . . ?
N7 Fe2 N6 85.28(6) . . ?
N5 Fe2 N6 79.43(6) . . ?
C1 O1 Fe1 127.43(11) . . ?
C19 O2 Fe1 120.43(11) . . ?
C20 O3 Fe2 129.75(11) . . ?
C38 O4 Fe2 123.57(11) . . ?
C2 O5 C39 117.90(14) . . ?
C18 O6 C41 114.80(13) . . ?
C37 O7 C43 113.27(13) . . ?
C7 N1 C8 121.46(16) . . ?
C7 N1 Fe1 124.58(13) . . ?
C8 N1 Fe1 113.04(11) . . ?
C10 N2 C9 110.79(14) . . ?
C10 N2 Fe1 116.84(11) . . ?
C9 N2 Fe1 107.89(11) . . ?
C13 N3 C12 118.77(15) . . ?
C13 N3 Fe1 122.18(12) . . ?
C12 N3 Fe1 118.95(11) . . ?
C47 N4 Fe1 172.88(15) . . ?
C26 N5 C27 120.95(16) . . ?
C26 N5 Fe2 126.11(13) . . ?
C27 N5 Fe2 112.92(12) . . ?
C28 N6 C29 111.21(14) . . ?
C28 N6 Fe2 107.53(11) . . ?
C29 N6 Fe2 117.02(11) . . ?
C32 N7 C31 118.17(15) . . ?
C32 N7 Fe2 122.97(12) . . ?
C31 N7 Fe2 118.81(11) . . ?
C48 N8 Fe2 171.31(15) . . ?
O1 C1 C6 123.66(16) . . ?
O1 C1 C2 118.67(16) . . ?
C6 C1 C2 117.63(16) . . ?
O5 C2 C3 124.34(17) . . ?
O5 C2 C1 114.53(15) . . ?
C3 C2 C1 121.08(17) . . ?
C2 C3 C4 120.55(18) . . ?
C5 C4 C3 119.76(17) . . ?
C4 C5 C6 121.06(18) . . ?
C5 C6 C1 119.89(17) . . ?
C5 C6 C7 116.99(16) . . ?
C1 C6 C7 123.11(16) . . ?
N1 C7 C6 125.00(17) . . ?
N1 C8 C9 106.69(15) . . ?
N2 C9 C8 109.00(15) . . ?
N2 C10 C11 114.66(15) . . ?
C10 C11 C12 116.51(15) . . ?
N3 C12 C11 109.10(15) . . ?
N3 C13 C14 124.41(17) . . ?
C15 C14 C19 120.06(17) . . ?
C15 C14 C13 118.68(16) . . ?
C19 C14 C13 120.87(16) . . ?
C16 C15 C14 120.60(17) . . ?
C15 C16 C17 119.86(17) . . ?
C18 C17 C16 120.59(18) . . ?
C17 C18 O6 119.39(16) . . ?
C17 C18 C19 121.11(17) . . ?
O6 C18 C19 119.32(16) . . ?
O2 C19 C18 119.81(16) . . ?
O2 C19 C14 122.54(16) . . ?
C18 C19 C14 117.63(16) . . ?
O3 C20 C25 123.90(16) . . ?
O3 C20 C21 118.94(16) . . ?
C25 C20 C21 117.16(16) . . ?
O8 C21 C22 124.10(17) . . ?
O8 C21 C20 114.83(15) . . ?
C22 C21 C20 121.07(17) . . ?
C21 C22 C23 120.51(18) . . ?
C24 C23 C22 120.00(17) . . ?
C23 C24 C25 120.87(18) . . ?
C24 C25 C20 120.15(17) . . ?
C24 C25 C26 116.91(17) . . ?
C20 C25 C26 122.93(16) . . ?
N5 C26 C25 125.48(17) . . ?
N5 C27 C28 106.77(15) . . ?
N6 C28 C27 108.66(15) . . ?
N6 C29 C30 113.26(15) . . ?
C29 C30 C31 115.58(16) . . ?
N7 C31 C30 109.48(15) . . ?
N7 C32 C33 124.84(16) . . ?
C34 C33 C38 120.30(17) . . ?
C34 C33 C32 118.33(16) . . ?
C38 C33 C32 121.04(16) . . ?
C35 C34 C33 120.91(17) . . ?
C34 C35 C36 119.52(17) . . ?
C37 C36 C35 120.35(18) . . ?
C36 C37 O7 119.80(16) . . ?
C36 C37 C38 121.71(17) . . ?
O7 C37 C38 118.46(15) . . ?
O4 C38 C33 123.19(16) . . ?
O4 C38 C37 119.64(16) . . ?
C33 C38 C37 117.16(16) . . ?
O5 C39 C40 112.84(17) . . ?
O6 C41 C42 108.96(15) . . ?
O7 C43 C44 107.98(15) . . ?
N4 C47 S1 178.02(17) . . ?
N8 C48 S2 178.73(18) . . ?
C21 O8 C45 116.77(14) . . ?
O8 C45 C46 107.65(15) . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 995955'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  to carry out CIF format checking respectively.
#
data_1@15

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis(3-methoxy-2-oxido-benzylidene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 Fe N4 O4 S'
_chemical_formula_weight         525.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0010 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.1820 0.2700 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0380 0.0360 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.165(3)
_cell_length_b                   11.6749(16)
_cell_length_c                   22.449(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.772(3)
_cell_angle_gamma                90
_cell_volume                     4783.3(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    15(2)
_cell_measurement_reflns_used    9231
_cell_measurement_theta_min      1.031
_cell_measurement_theta_max      14.385

_exptl_crystal_description       block
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             2200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.744
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      15(2)
_diffrn_radiation_wavelength     0.38745
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'APS Beamline 15-ID-B'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'fine-slice ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            106433
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.031
_diffrn_reflns_theta_max         14.385
_diffrn_reflns_theta_full        13.443
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10543
_reflns_number_gt                8039
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0252P)²+4.5683P] 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         10543
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.70998(2) 0.23287(3) 0.89047(2) 0.00444(7) Uani 1 1 d . . . . .
Fe2 Fe 0.79954(2) 0.72955(2) 1.09424(2) 0.00457(7) Uani 1 1 d . . . . .
S1 S 0.57208(3) 0.43263(5) 0.70873(2) 0.00840(11) Uani 1 1 d . . . . .
S2 S 0.93759(3) 0.52997(5) 1.27453(2) 0.00831(11) Uani 1 1 d . . . . .
O1 O 0.78745(8) 0.33383(12) 0.88893(6) 0.0067(3) Uani 1 1 d . . . . .
O2 O 0.76929(7) 0.15218(12) 0.95912(6) 0.0062(3) Uani 1 1 d . . . . .
O3 O 0.72577(8) 0.61950(12) 1.09539(6) 0.0066(3) Uani 1 1 d . . . . .
O4 O 0.74130(7) 0.80065(12) 1.02159(6) 0.0062(3) Uani 1 1 d . . . . .
O5 O 0.86731(8) 0.51317(12) 0.88436(7) 0.0077(3) Uani 1 1 d . . . . .
O6 O 0.90058(8) 0.05059(12) 1.02122(6) 0.0070(3) Uani 1 1 d . . . . .
O7 O 0.61194(8) 0.88588(12) 0.94855(7) 0.0076(3) Uani 1 1 d . . . . .
N1 N 0.73508(9) 0.12062(14) 0.83781(8) 0.0053(3) Uani 1 1 d . . . . .
N2 N 0.62718(9) 0.12553(15) 0.88871(8) 0.0065(3) Uani 1 1 d . . . . .
H2 H 0.6427 0.0805 0.9285 0.008 Uiso 1 1 calc R U . . .
N3 N 0.68174(9) 0.33576(14) 0.94803(8) 0.0057(3) Uani 1 1 d . . . . .
N4 N 0.64727(9) 0.31029(15) 0.81676(8) 0.0069(3) Uani 1 1 d . . . . .
N5 N 0.76220(9) 0.84416(14) 1.13801(8) 0.0063(3) Uani 1 1 d . . . . .
N6 N 0.88065(9) 0.84297(14) 1.10024(8) 0.0065(3) Uani 1 1 d . . . . .
H6 H 0.8684 0.8839 1.0592 0.008 Uiso 1 1 calc R U . . .
N7 N 0.83974(9) 0.62762(14) 1.04341(8) 0.0058(3) Uani 1 1 d . . . . .
N8 N 0.85961(9) 0.66224(15) 1.17190(8) 0.0074(4) Uani 1 1 d . . . . .
C1 C 0.82096(11) 0.33126(18) 0.84580(9) 0.0066(4) Uani 1 1 d . . . . .
C2 C 0.86508(11) 0.42817(17) 0.84150(9) 0.0070(4) Uani 1 1 d . . . . .
C3 C 0.90354(11) 0.43126(18) 0.79862(9) 0.0073(4) Uani 1 1 d . . . . .
H3 H 0.9330 0.4960 0.7972 0.009 Uiso 1 1 calc R U . . .
C4 C 0.89953(11) 0.33960(18) 0.75697(10) 0.0084(4) Uani 1 1 d . . . . .
H4 H 0.9258 0.3427 0.7273 0.010 Uiso 1 1 calc R U . . .
C5 C 0.85741(11) 0.24579(18) 0.75947(9) 0.0078(4) Uani 1 1 d . . . . .
H5 H 0.8544 0.1842 0.7312 0.009 Uiso 1 1 calc R U . . .
C6 C 0.81844(11) 0.23970(18) 0.80360(9) 0.0071(4) Uani 1 1 d . . . . .
C7 C 0.77782(11) 0.13579(18) 0.80419(9) 0.0068(4) Uani 1 1 d . . . . .
H7 H 0.7830 0.0746 0.7780 0.008 Uiso 1 1 calc R U . . .
C8 C 0.69671(11) 0.01128(17) 0.83730(10) 0.0072(4) Uani 1 1 d . . . . .
H8A H 0.7214 -0.0343 0.8750 0.009 Uiso 1 1 calc R U . . .
H8B H 0.6956 -0.0341 0.7998 0.009 Uiso 1 1 calc R U . . .
C9 C 0.61993(11) 0.04297(18) 0.83649(9) 0.0074(4) Uani 1 1 d . . . . .
H9A H 0.5930 0.0786 0.7960 0.009 Uiso 1 1 calc R U . . .
H9B H 0.5928 -0.0261 0.8424 0.009 Uiso 1 1 calc R U . . .
C10 C 0.55483(11) 0.17722(18) 0.88404(10) 0.0080(4) Uani 1 1 d . . . . .
H10A H 0.5208 0.1155 0.8875 0.010 Uiso 1 1 calc R U . . .
H10B H 0.5347 0.2126 0.8422 0.010 Uiso 1 1 calc R U . . .
C11 C 0.55728(11) 0.26768(18) 0.93376(10) 0.0080(4) Uani 1 1 d . . . . .
H11A H 0.5760 0.2315 0.9755 0.010 Uiso 1 1 calc R U . . .
H11B H 0.5067 0.2939 0.9286 0.010 Uiso 1 1 calc R U . . .
C12 C 0.60466(11) 0.37224(18) 0.93205(10) 0.0068(4) Uani 1 1 d . . . . .
H12A H 0.5889 0.4069 0.8898 0.008 Uiso 1 1 calc R U . . .
H12B H 0.5991 0.4304 0.9624 0.008 Uiso 1 1 calc R U . . .
C13 C 0.72464(11) 0.36340(17) 1.00243(9) 0.0066(4) Uani 1 1 d . . . . .
H13 H 0.7087 0.4209 1.0252 0.008 Uiso 1 1 calc R U . . .
C14 C 0.79586(11) 0.31185(17) 1.03091(9) 0.0059(4) Uani 1 1 d . . . . .
C15 C 0.84162(11) 0.35804(17) 1.08708(9) 0.0066(4) Uani 1 1 d . . . . .
H15 H 0.8273 0.4259 1.1036 0.008 Uiso 1 1 calc R U . . .
C16 C 0.90706(11) 0.30609(18) 1.11855(9) 0.0074(4) Uani 1 1 d . . . . .
H16 H 0.9380 0.3384 1.1562 0.009 Uiso 1 1 calc R U . . .
C17 C 0.92764(11) 0.20502(17) 1.09447(9) 0.0076(4) Uani 1 1 d . . . . .
H17 H 0.9734 0.1703 1.1152 0.009 Uiso 1 1 calc R U . . .
C18 C 0.88173(11) 0.15581(17) 1.04086(9) 0.0063(4) Uani 1 1 d . . . . .
C19 C 0.81375(11) 0.20701(17) 1.00781(9) 0.0066(4) Uani 1 1 d . . . . .
C20 C 0.68319(11) 0.62639(18) 1.13136(9) 0.0058(4) Uani 1 1 d . . . . .
C21 C 0.64568(11) 0.52479(17) 1.14096(9) 0.0065(4) Uani 1 1 d . . . . .
C22 C 0.59452(11) 0.52855(18) 1.17295(9) 0.0078(4) Uani 1 1 d . . . . .
H22 H 0.5678 0.4614 1.1759 0.009 Uiso 1 1 calc R U . . .
C23 C 0.58142(11) 0.63034(18) 1.20122(9) 0.0081(4) Uani 1 1 d . . . . .
H23 H 0.5462 0.6320 1.2232 0.010 Uiso 1 1 calc R U . . .
C24 C 0.61988(11) 0.72688(18) 1.19676(9) 0.0080(4) Uani 1 1 d . . . . .
H24 H 0.6123 0.7951 1.2170 0.010 Uiso 1 1 calc R U . . .
C25 C 0.67088(11) 0.72694(18) 1.16247(9) 0.0072(4) Uani 1 1 d . . . . .
C26 C 0.70996(11) 0.83227(18) 1.16229(9) 0.0074(4) Uani 1 1 d . . . . .
H26 H 0.6962 0.8974 1.1814 0.009 Uiso 1 1 calc R U . . .
C27 C 0.79822(11) 0.95569(17) 1.13933(10) 0.0071(4) Uani 1 1 d . . . . .
H27A H 0.7930 1.0031 1.1743 0.008 Uiso 1 1 calc R U . . .
H27B H 0.7764 0.9975 1.0996 0.008 Uiso 1 1 calc R U . . .
C28 C 0.87822(11) 0.92945(18) 1.14823(10) 0.0075(4) Uani 1 1 d . . . . .
H28A H 0.9044 0.9999 1.1429 0.009 Uiso 1 1 calc R U . . .
H28B H 0.9018 0.8988 1.1907 0.009 Uiso 1 1 calc R U . . .
C29 C 0.95678(11) 0.79749(17) 1.11340(10) 0.0077(4) Uani 1 1 d . . . . .
H29A H 0.9726 0.7641 1.1560 0.009 Uiso 1 1 calc R U . . .
H29B H 0.9902 0.8618 1.1127 0.009 Uiso 1 1 calc R U . . .
C30 C 0.96370(11) 0.70686(18) 1.06684(10) 0.0081(4) Uani 1 1 d . . . . .
H30A H 1.0159 0.6850 1.0767 0.010 Uiso 1 1 calc R U . . .
H30B H 0.9483 0.7408 1.0244 0.010 Uiso 1 1 calc R U . . .
C31 C 0.91851(11) 0.59853(17) 1.06622(10) 0.0073(4) Uani 1 1 d . . . . .
H31A H 0.9300 0.5403 1.0385 0.009 Uiso 1 1 calc R U . . .
H31B H 0.9308 0.5662 1.1089 0.009 Uiso 1 1 calc R U . . .
C32 C 0.80428(11) 0.59591(17) 0.98752(9) 0.0071(4) Uani 1 1 d . . . . .
H32 H 0.8260 0.5391 0.9686 0.009 Uiso 1 1 calc R U . . .
C33 C 0.73366(11) 0.64064(17) 0.95145(9) 0.0067(4) Uani 1 1 d . . . . .
C34 C 0.69648(11) 0.58961(18) 0.89359(10) 0.0080(4) Uani 1 1 d . . . . .
H34 H 0.7162 0.5230 0.8805 0.010 Uiso 1 1 calc R U . . .
C35 C 0.63162(11) 0.63535(18) 0.85563(10) 0.0091(4) Uani 1 1 d . . . . .
H35 H 0.6068 0.6002 0.8168 0.011 Uiso 1 1 calc R U . . .
C36 C 0.60295(11) 0.73354(18) 0.87487(9) 0.0080(4) Uani 1 1 d . . . . .
H36 H 0.5579 0.7643 0.8493 0.010 Uiso 1 1 calc R U . . .
C37 C 0.63945(11) 0.78640(17) 0.93065(10) 0.0071(4) Uani 1 1 d . . . . .
C38 C 0.70683(11) 0.74258(17) 0.97035(9) 0.0063(4) Uani 1 1 d . . . . .
C39 C 0.89369(12) 0.62449(18) 0.87387(10) 0.0106(4) Uani 1 1 d . . . . .
H39A H 0.9416 0.6158 0.8662 0.013 Uiso 1 1 calc R U . . .
H39B H 0.9014 0.6716 0.9120 0.013 Uiso 1 1 calc R U . . .
C40 C 0.84150(13) 0.68622(19) 0.81906(11) 0.0144(5) Uani 1 1 d . . . . .
H40A H 0.8357 0.6420 0.7807 0.022 Uiso 1 1 calc R U . . .
H40B H 0.8612 0.7622 0.8147 0.022 Uiso 1 1 calc R U . . .
H40C H 0.7938 0.6945 0.8262 0.022 Uiso 1 1 calc R U . . .
C41 C 0.90916(11) 0.05252(18) 0.95901(9) 0.0077(4) Uani 1 1 d . . . . .
H41A H 0.9602 0.0733 0.9618 0.009 Uiso 1 1 calc R U . . .
H41B H 0.8759 0.1104 0.9328 0.009 Uiso 1 1 calc R U . . .
C42 C 0.89124(12) -0.06421(18) 0.93007(10) 0.0103(4) Uani 1 1 d . . . . .
H42A H 0.9282 -0.1193 0.9532 0.015 Uiso 1 1 calc R U . . .
H42B H 0.8910 -0.0614 0.8864 0.015 Uiso 1 1 calc R U . . .
H42C H 0.8428 -0.0879 0.9318 0.015 Uiso 1 1 calc R U . . .
C43 C 0.58599(11) 0.86812(18) 1.00202(10) 0.0088(4) Uani 1 1 d . . . . .
H43A H 0.6151 0.8075 1.0294 0.011 Uiso 1 1 calc R U . . .
H43B H 0.5340 0.8441 0.9880 0.011 Uiso 1 1 calc R U . . .
C44 C 0.59416(12) 0.97964(18) 1.03706(10) 0.0102(4) Uani 1 1 d . . . . .
H44A H 0.6459 1.0022 1.0510 0.015 Uiso 1 1 calc R U . . .
H44B H 0.5767 0.9704 1.0735 0.015 Uiso 1 1 calc R U . . .
H44C H 0.5653 1.0390 1.0095 0.015 Uiso 1 1 calc R U . . .
C47 C 0.61666(11) 0.36115(18) 0.77153(10) 0.0074(4) Uani 1 1 d . . . . .
C48 C 0.89158(11) 0.60751(17) 1.21506(10) 0.0067(4) Uani 1 1 d . . . . .
O8 O 0.66489(8) 0.42597(12) 1.11671(7) 0.0081(3) Uani 1 1 d . . . . .
C45 C 0.64235(12) 0.32008(18) 1.13831(10) 0.0096(4) Uani 1 1 d . . . . .
H45A H 0.5893 0.3074 1.1178 0.012 Uiso 1 1 calc R U . . .
H45B H 0.6512 0.3234 1.1841 0.012 Uiso 1 1 calc R U . . .
C46 C 0.68588(12) 0.22344(18) 1.12243(10) 0.0109(4) Uani 1 1 d . . . . .
H46A H 0.6744 0.2177 1.0769 0.016 Uiso 1 1 calc R U . . .
H46B H 0.6731 0.1514 1.1389 0.016 Uiso 1 1 calc R U . . .
H46C H 0.7383 0.2385 1.1411 0.016 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
Fe1 O2 1.8668(14) . ?
Fe1 O1 1.9042(14) . ?
Fe1 N1 1.9217(17) . ?
Fe1 N4 1.9457(18) . ?
Fe1 N3 1.9578(17) . ?
Fe1 N2 2.0130(17) . ?
Fe2 O4 1.8665(14) . ?
Fe2 O3 1.9164(14) . ?
Fe2 N5 1.9228(17) . ?
Fe2 N8 1.9383(18) . ?
Fe2 N7 1.9618(17) . ?
Fe2 N6 2.0149(17) . ?
S1 C47 1.637(2) . ?
S2 C48 1.631(2) . ?
O1 C1 1.315(2) . ?
O2 C19 1.327(2) . ?
O3 C20 1.314(2) . ?
O4 C38 1.325(2) . ?
O5 C2 1.374(2) . ?
O5 C39 1.440(2) . ?
O6 C18 1.390(2) . ?
O6 C41 1.455(2) . ?
O7 C37 1.385(2) . ?
O7 C43 1.448(2) . ?
N1 C7 1.284(3) . ?
N1 C8 1.471(3) . ?
N2 C10 1.486(3) . ?
N2 C9 1.491(3) . ?
N3 C13 1.288(3) . ?
N3 C12 1.473(2) . ?
N4 C47 1.168(3) . ?
N5 C26 1.285(3) . ?
N5 C27 1.470(3) . ?
N6 C28 1.488(3) . ?
N6 C29 1.495(3) . ?
N7 C32 1.285(3) . ?
N7 C31 1.478(3) . ?
N8 C48 1.166(3) . ?
C1 C6 1.419(3) . ?
C1 C2 1.433(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.408(3) . ?
C4 C5 1.372(3) . ?
C5 C6 1.413(3) . ?
C6 C7 1.444(3) . ?
C8 C9 1.512(3) . ?
C10 C11 1.527(3) . ?
C11 C12 1.529(3) . ?
C13 C14 1.450(3) . ?
C14 C15 1.405(3) . ?
C14 C19 1.412(3) . ?
C15 C16 1.378(3) . ?
C16 C17 1.404(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.420(3) . ?
C20 C25 1.422(3) . ?
C20 C21 1.437(3) . ?
C21 O8 1.373(2) . ?
C21 C22 1.382(3) . ?
C22 C23 1.405(3) . ?
C23 C24 1.367(3) . ?
C24 C25 1.417(3) . ?
C25 C26 1.440(3) . ?
C27 C28 1.516(3) . ?
C29 C30 1.521(3) . ?
C30 C31 1.531(3) . ?
C32 C33 1.446(3) . ?
C33 C34 1.409(3) . ?
C33 C38 1.412(3) . ?
C34 C35 1.382(3) . ?
C35 C36 1.396(3) . ?
C36 C37 1.380(3) . ?
C37 C38 1.422(3) . ?
C39 C40 1.511(3) . ?
C41 C42 1.504(3) . ?
C43 C44 1.504(3) . ?
O8 C45 1.441(2) . ?
C45 C46 1.509(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Fe1 O1 92.62(6) . . ?
O2 Fe1 N1 87.71(7) . . ?
O1 Fe1 N1 93.90(7) . . ?
O2 Fe1 N4 177.33(7) . . ?
O1 Fe1 N4 88.83(7) . . ?
N1 Fe1 N4 89.96(7) . . ?
O2 Fe1 N3 89.20(7) . . ?
O1 Fe1 N3 90.36(7) . . ?
N1 Fe1 N3 174.84(7) . . ?
N4 Fe1 N3 93.03(7) . . ?
O2 Fe1 N2 88.84(7) . . ?
O1 Fe1 N2 177.92(7) . . ?
N1 Fe1 N2 84.68(7) . . ?
N4 Fe1 N2 89.65(7) . . ?
N3 Fe1 N2 91.13(7) . . ?
O4 Fe2 O3 93.62(6) . . ?
O4 Fe2 N5 85.44(7) . . ?
O3 Fe2 N5 93.93(7) . . ?
O4 Fe2 N8 177.27(7) . . ?
O3 Fe2 N8 87.37(7) . . ?
N5 Fe2 N8 91.95(7) . . ?
O4 Fe2 N7 89.87(7) . . ?
O3 Fe2 N7 91.35(7) . . ?
N5 Fe2 N7 173.15(7) . . ?
N8 Fe2 N7 92.66(7) . . ?
O4 Fe2 N6 90.54(7) . . ?
O3 Fe2 N6 175.52(7) . . ?
N5 Fe2 N6 84.75(7) . . ?
N8 Fe2 N6 88.40(7) . . ?
N7 Fe2 N6 90.32(7) . . ?
C1 O1 Fe1 123.90(13) . . ?
C19 O2 Fe1 120.83(13) . . ?
C20 O3 Fe2 124.49(13) . . ?
C38 O4 Fe2 122.53(13) . . ?
C2 O5 C39 118.35(15) . . ?
C18 O6 C41 114.03(15) . . ?
C37 O7 C43 112.22(15) . . ?
C7 N1 C8 121.45(17) . . ?
C7 N1 Fe1 126.28(15) . . ?
C8 N1 Fe1 112.22(12) . . ?
C10 N2 C9 110.24(15) . . ?
C10 N2 Fe1 117.48(13) . . ?
C9 N2 Fe1 107.55(12) . . ?
C13 N3 C12 117.45(17) . . ?
C13 N3 Fe1 123.69(14) . . ?
C12 N3 Fe1 118.39(13) . . ?
C47 N4 Fe1 172.54(17) . . ?
C26 N5 C27 120.60(18) . . ?
C26 N5 Fe2 126.95(15) . . ?
C27 N5 Fe2 112.39(13) . . ?
C28 N6 C29 110.02(15) . . ?
C28 N6 Fe2 107.48(12) . . ?
C29 N6 Fe2 117.80(13) . . ?
C32 N7 C31 116.85(17) . . ?
C32 N7 Fe2 123.92(14) . . ?
C31 N7 Fe2 118.61(13) . . ?
C48 N8 Fe2 170.61(17) . . ?
O1 C1 C6 125.72(18) . . ?
O1 C1 C2 117.53(18) . . ?
C6 C1 C2 116.75(18) . . ?
O5 C2 C3 124.10(18) . . ?
O5 C2 C1 114.58(17) . . ?
C3 C2 C1 121.28(19) . . ?
C2 C3 C4 120.73(19) . . ?
C5 C4 C3 119.56(19) . . ?
C4 C5 C6 120.83(19) . . ?
C5 C6 C1 120.84(19) . . ?
C5 C6 C7 116.79(18) . . ?
C1 C6 C7 122.36(18) . . ?
N1 C7 C6 124.31(19) . . ?
N1 C8 C9 105.66(16) . . ?
N2 C9 C8 106.97(16) . . ?
N2 C10 C11 114.17(17) . . ?
C10 C11 C12 114.83(17) . . ?
N3 C12 C11 108.80(16) . . ?
N3 C13 C14 123.83(19) . . ?
C15 C14 C19 120.48(19) . . ?
C15 C14 C13 118.83(18) . . ?
C19 C14 C13 119.97(18) . . ?
C16 C15 C14 120.81(19) . . ?
C15 C16 C17 119.42(19) . . ?
C18 C17 C16 120.42(19) . . ?
C17 C18 O6 119.09(18) . . ?
C17 C18 C19 121.29(19) . . ?
O6 C18 C19 119.50(18) . . ?
O2 C19 C14 123.63(18) . . ?
O2 C19 C18 118.90(18) . . ?
C14 C19 C18 117.40(18) . . ?
O3 C20 C25 125.42(18) . . ?
O3 C20 C21 118.33(18) . . ?
C25 C20 C21 116.25(18) . . ?
O8 C21 C22 123.47(18) . . ?
O8 C21 C20 115.29(17) . . ?
C22 C21 C20 121.23(19) . . ?
C21 C22 C23 120.97(19) . . ?
C24 C23 C22 119.30(19) . . ?
C23 C24 C25 121.1(2) . . ?
C24 C25 C20 120.78(19) . . ?
C24 C25 C26 116.58(19) . . ?
C20 C25 C26 122.63(18) . . ?
N5 C26 C25 124.49(19) . . ?
N5 C27 C28 105.87(16) . . ?
N6 C28 C27 107.20(16) . . ?
N6 C29 C30 113.32(16) . . ?
C29 C30 C31 114.41(17) . . ?
N7 C31 C30 109.18(16) . . ?
N7 C32 C33 124.62(19) . . ?
C34 C33 C38 120.35(19) . . ?
C34 C33 C32 119.16(19) . . ?
C38 C33 C32 120.03(19) . . ?
C35 C34 C33 120.78(19) . . ?
C34 C35 C36 119.44(19) . . ?
C37 C36 C35 120.66(19) . . ?
C36 C37 O7 120.40(18) . . ?
C36 C37 C38 121.33(19) . . ?
O7 C37 C38 118.25(18) . . ?
O4 C38 C33 124.15(18) . . ?
O4 C38 C37 118.49(18) . . ?
C33 C38 C37 117.34(18) . . ?
O5 C39 C40 112.68(18) . . ?
O6 C41 C42 108.83(16) . . ?
O7 C43 C44 107.60(17) . . ?
N4 C47 S1 178.66(19) . . ?
N8 C48 S2 178.66(19) . . ?
C21 O8 C45 116.30(15) . . ?
O8 C45 C46 108.53(16) . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.074

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 995956'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1@298K

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis(3-methoxy-2-oxido-benzylidene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H29 Fe N4 O4 S'
_chemical_formula_weight         525.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.3340(7)
_cell_length_b                   11.4560(3)
_cell_length_c                   23.8310(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.131(4)
_cell_angle_gamma                90
_cell_volume                     5044.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    10429
_cell_measurement_theta_min      2.5777
_cell_measurement_theta_max      27.8057

_exptl_crystal_description       prism
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             2200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.718
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_detector_area_resol_mean 8.4012
_diffrn_reflns_number            20832
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.081
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             10146
_reflns_number_gt                6359
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_structure_solution    'SIR-2011 (Burla et al., 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0254P)²+5.0366P] 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         10146
_refine_ls_number_parameters     628
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.71603(2) 0.23728(4) 0.89421(2) 0.04018(13) Uani 1 1 d . . . . .
Fe2 Fe 0.79716(3) 0.71317(4) 1.08867(2) 0.04357(14) Uani 1 1 d . . . . .
S1 S 0.57163(7) 0.42958(10) 0.71792(5) 0.0805(4) Uani 1 1 d . . . . .
S2 S 0.93562(6) 0.54932(11) 1.27341(5) 0.0827(4) Uani 1 1 d . . . . .
O1 O 0.79869(11) 0.32186(18) 0.88744(9) 0.0442(5) Uani 1 1 d . . . . .
O2 O 0.76954(11) 0.15017(17) 0.96313(9) 0.0404(5) Uani 1 1 d . . . . .
O3 O 0.71649(13) 0.62365(19) 1.09590(10) 0.0522(6) Uani 1 1 d . . . . .
O4 O 0.74284(12) 0.79349(18) 1.01771(9) 0.0447(5) Uani 1 1 d . . . . .
O5 O 0.87672(13) 0.5046(2) 0.87791(10) 0.0595(7) Uani 1 1 d . . . . .
O6 O 0.90163(12) 0.0551(2) 1.02203(10) 0.0532(6) Uani 1 1 d . . . . .
O7 O 0.61335(14) 0.8817(2) 0.95089(11) 0.0640(7) Uani 1 1 d . . . . .
N1 N 0.73764(15) 0.1099(2) 0.83921(12) 0.0461(7) Uani 1 1 d . . . . .
N2 N 0.62358(14) 0.1198(2) 0.88429(13) 0.0522(8) Uani 1 1 d . . . . .
H2 H 0.6349 0.0713 0.9197 0.063 Uiso 1 1 calc R U . . .
N3 N 0.67653(15) 0.3312(2) 0.95276(13) 0.0457(7) Uani 1 1 d . . . . .
N4 N 0.65060(16) 0.3252(2) 0.82150(13) 0.0540(8) Uani 1 1 d . . . . .
N5 N 0.76718(17) 0.8462(2) 1.13663(13) 0.0535(8) Uani 1 1 d . . . . .
N6 N 0.88808(15) 0.8352(2) 1.09947(12) 0.0535(8) Uani 1 1 d . . . . .
H6 H 0.8777 0.8806 1.0631 0.064 Uiso 1 1 calc R U . . .
N7 N 0.84326(15) 0.6214(2) 1.03326(12) 0.0455(7) Uani 1 1 d . . . . .
N8 N 0.86167(17) 0.6322(3) 1.16344(13) 0.0621(9) Uani 1 1 d . . . . .
C1 C 0.82679(17) 0.3223(3) 0.84333(14) 0.0393(8) Uani 1 1 d . . . . .
C2 C 0.86921(18) 0.4189(3) 0.83683(15) 0.0463(8) Uani 1 1 d . . . . .
C3 C 0.9020(2) 0.4204(3) 0.79276(16) 0.0594(10) Uani 1 1 d . . . . .
H3 H 0.9305 0.4839 0.7894 0.071 Uiso 1 1 calc R U . . .
C4 C 0.8933(2) 0.3295(4) 0.75365(18) 0.0698(12) Uani 1 1 d . . . . .
H4 H 0.9156 0.3321 0.7241 0.084 Uiso 1 1 calc R U . . .
C5 C 0.8521(2) 0.2361(3) 0.75810(16) 0.0635(11) Uani 1 1 d . . . . .
H5 H 0.8463 0.1753 0.7313 0.076 Uiso 1 1 calc R U . . .
C6 C 0.81805(19) 0.2299(3) 0.80295(14) 0.0471(8) Uani 1 1 d . . . . .
C7 C 0.7765(2) 0.1266(3) 0.80489(15) 0.0530(9) Uani 1 1 d . . . . .
H7 H 0.7781 0.0667 0.7789 0.064 Uiso 1 1 calc R U . . .
C8 C 0.6955(2) 0.0032(3) 0.83682(17) 0.0603(10) Uani 1 1 d . . . . .
H8A H 0.7165 -0.0444 0.8713 0.072 Uiso 1 1 calc R U . . .
H8B H 0.6948 -0.0420 0.8022 0.072 Uiso 1 1 calc R U . . .
C9 C 0.6201(2) 0.0403(3) 0.83446(17) 0.0619(11) Uani 1 1 d . . . . .
H9A H 0.5975 0.0798 0.7976 0.074 Uiso 1 1 calc R U . . .
H9B H 0.5912 -0.0278 0.8368 0.074 Uiso 1 1 calc R U . . .
C10 C 0.55259(19) 0.1741(4) 0.87829(18) 0.0652(11) Uani 1 1 d . . . . .
H10A H 0.5174 0.1129 0.8767 0.078 Uiso 1 1 calc R U . . .
H10B H 0.5374 0.2163 0.8414 0.078 Uiso 1 1 calc R U . . .
C11 C 0.55223(19) 0.2570(4) 0.92741(18) 0.0673(11) Uani 1 1 d . . . . .
H11A H 0.5673 0.2138 0.9640 0.081 Uiso 1 1 calc R U . . .
H11B H 0.5027 0.2820 0.9218 0.081 Uiso 1 1 calc R U . . .
C12 C 0.59967(19) 0.3662(3) 0.93430(17) 0.0600(10) Uani 1 1 d . . . . .
H12A H 0.5885 0.4079 0.8973 0.072 Uiso 1 1 calc R U . . .
H12B H 0.5901 0.4177 0.9635 0.072 Uiso 1 1 calc R U . . .
C13 C 0.7156(2) 0.3544(3) 1.00533(16) 0.0484(9) Uani 1 1 d . . . . .
H13 H 0.6971 0.4065 1.0271 0.058 Uiso 1 1 calc R U . . .
C14 C 0.78657(18) 0.3051(3) 1.03302(13) 0.0421(8) Uani 1 1 d . . . . .
C15 C 0.8288(2) 0.3525(3) 1.08625(15) 0.0544(10) Uani 1 1 d . . . . .
H15 H 0.8119 0.4168 1.1021 0.065 Uiso 1 1 calc R U . . .
C16 C 0.8945(2) 0.3055(3) 1.11508(15) 0.0591(10) Uani 1 1 d . . . . .
H16 H 0.9226 0.3386 1.1500 0.071 Uiso 1 1 calc R U . . .
C17 C 0.9193(2) 0.2085(3) 1.09226(15) 0.0538(9) Uani 1 1 d . . . . .
H17 H 0.9645 0.1777 1.1116 0.065 Uiso 1 1 calc R U . . .
C18 C 0.87787(18) 0.1572(3) 1.04122(14) 0.0435(8) Uani 1 1 d . . . . .
C19 C 0.80964(17) 0.2039(3) 1.01036(13) 0.0383(8) Uani 1 1 d . . . . .
C20 C 0.67871(18) 0.6340(3) 1.13356(14) 0.0476(9) Uani 1 1 d . . . . .
C21 C 0.6364(2) 0.5372(3) 1.14157(16) 0.0623(10) Uani 1 1 d D . . . .
C22 C 0.5928(2) 0.5471(4) 1.17787(19) 0.0743(12) Uani 1 1 d . . . . .
H22 H 0.5647 0.4838 1.1822 0.089 Uiso 1 1 calc R U . . .
C23 C 0.5900(2) 0.6481(5) 1.20757(19) 0.0779(14) Uani 1 1 d . . . . .
H23 H 0.5598 0.6532 1.2314 0.094 Uiso 1 1 calc R U . . .
C24 C 0.6314(2) 0.7415(4) 1.20241(16) 0.0670(12) Uani 1 1 d . . . . .
H24 H 0.6296 0.8096 1.2232 0.080 Uiso 1 1 calc R U . . .
C25 C 0.6768(2) 0.7360(3) 1.16589(15) 0.0513(9) Uani 1 1 d . . . . .
C26 C 0.7197(2) 0.8371(3) 1.16392(16) 0.0592(10) Uani 1 1 d . . . . .
H26 H 0.7122 0.9025 1.1845 0.071 Uiso 1 1 calc R U . . .
C27 C 0.8086(2) 0.9537(3) 1.13861(18) 0.0705(12) Uani 1 1 d . . . . .
H27A H 0.8055 1.0024 1.1711 0.085 Uiso 1 1 calc R U . . .
H27B H 0.7899 0.9973 1.1024 0.085 Uiso 1 1 calc R U . . .
C28 C 0.8859(2) 0.9183(3) 1.14654(17) 0.0703(12) Uani 1 1 d . . . . .
H28A H 0.9147 0.9867 1.1447 0.084 Uiso 1 1 calc R U . . .
H28B H 0.9058 0.8819 1.1846 0.084 Uiso 1 1 calc R U . . .
C29 C 0.9609(2) 0.7843(4) 1.10926(18) 0.0677(11) Uani 1 1 d . . . . .
H29A H 0.9743 0.7432 1.1465 0.081 Uiso 1 1 calc R U . . .
H29B H 0.9954 0.8471 1.1121 0.081 Uiso 1 1 calc R U . . .
C30 C 0.9664(2) 0.7012(4) 1.06166(18) 0.0683(12) Uani 1 1 d . . . . .
H30A H 1.0167 0.6782 1.0696 0.082 Uiso 1 1 calc R U . . .
H30B H 0.9527 0.7429 1.0246 0.082 Uiso 1 1 calc R U . . .
C31 C 0.92051(19) 0.5906(3) 1.05449(17) 0.0606(10) Uani 1 1 d . . . . .
H31A H 0.9326 0.5385 1.0267 0.073 Uiso 1 1 calc R U . . .
H31B H 0.9306 0.5505 1.0919 0.073 Uiso 1 1 calc R U . . .
C32 C 0.8078(2) 0.5960(3) 0.97986(16) 0.0476(9) Uani 1 1 d . . . . .
H32 H 0.8294 0.5441 0.9601 0.057 Uiso 1 1 calc R U . . .
C33 C 0.73785(18) 0.6409(3) 0.94814(14) 0.0429(8) Uani 1 1 d . . . . .
C34 C 0.7012(2) 0.5924(3) 0.89352(16) 0.0585(10) Uani 1 1 d . . . . .
H34 H 0.7212 0.5287 0.8798 0.070 Uiso 1 1 calc R U . . .
C35 C 0.6372(2) 0.6364(3) 0.86027(17) 0.0653(11) Uani 1 1 d . . . . .
H35 H 0.6136 0.6028 0.8242 0.078 Uiso 1 1 calc R U . . .
C36 C 0.6072(2) 0.7314(3) 0.88021(16) 0.0612(10) Uani 1 1 d . . . . .
H36 H 0.5628 0.7607 0.8578 0.073 Uiso 1 1 calc R U . . .
C37 C 0.64253(19) 0.7832(3) 0.93311(15) 0.0491(9) Uani 1 1 d . . . . .
C38 C 0.70926(17) 0.7398(3) 0.96852(14) 0.0402(8) Uani 1 1 d . . . . .
C39 C 0.8992(3) 0.6189(4) 0.8653(2) 0.0898(16) Uani 1 1 d . . . . .
H39A H 0.9423 0.6117 0.8527 0.108 Uiso 1 1 calc R U . . .
H39B H 0.9115 0.6652 0.9010 0.108 Uiso 1 1 calc R U . . .
C40 C 0.8427(4) 0.6795(4) 0.8197(3) 0.126(2) Uani 1 1 d . . . . .
H40A H 0.8302 0.6340 0.7843 0.189 Uiso 1 1 calc R U . . .
H40B H 0.8605 0.7544 0.8121 0.189 Uiso 1 1 calc R U . . .
H40C H 0.8007 0.6899 0.8327 0.189 Uiso 1 1 calc R U . . .
C41 C 0.9096(2) 0.0595(3) 0.96347(16) 0.0591(10) Uani 1 1 d . . . . .
H41A H 0.9597 0.0755 0.9658 0.071 Uiso 1 1 calc R U . . .
H41B H 0.8798 0.1216 0.9411 0.071 Uiso 1 1 calc R U . . .
C42 C 0.8873(3) -0.0536(4) 0.93393(18) 0.0859(14) Uani 1 1 d . . . . .
H42A H 0.9190 -0.1140 0.9548 0.129 Uiso 1 1 calc R U . . .
H42B H 0.8899 -0.0496 0.8944 0.129 Uiso 1 1 calc R U . . .
H42C H 0.8386 -0.0708 0.9334 0.129 Uiso 1 1 calc R U . . .
C43 C 0.5901(2) 0.8622(4) 1.0031(2) 0.0802(13) Uani 1 1 d . . . . .
H43A H 0.6188 0.8009 1.0270 0.096 Uiso 1 1 calc R U . . .
H43B H 0.5397 0.8386 0.9918 0.096 Uiso 1 1 calc R U . . .
C44 C 0.5995(3) 0.9716(4) 1.0363(2) 0.1052(17) Uani 1 1 d . . . . .
H44A H 0.6491 0.9958 1.0459 0.158 Uiso 1 1 calc R U . . .
H44B H 0.5865 0.9599 1.0718 0.158 Uiso 1 1 calc R U . . .
H44C H 0.5691 1.0307 1.0130 0.158 Uiso 1 1 calc R U . . .
C47 C 0.61827(18) 0.3676(3) 0.77800(15) 0.0442(8) Uani 1 1 d . . . . .
C48 C 0.89220(19) 0.5989(3) 1.20949(16) 0.0473(9) Uani 1 1 d . . . . .
O8B O 0.6306(14) 0.4561(10) 1.0984(6) 0.0817(19) Uani 0.256(8) 1 d D U P A 2
C45B C 0.6049(14) 0.3404(13) 1.1046(9) 0.114(3) Uani 0.256(8) 1 d D U P A 2
H45A H 0.6012 0.2937 1.0699 0.136 Uiso 0.256(8) 1 calc R U P A 2
H45B H 0.5582 0.3425 1.1120 0.136 Uiso 0.256(8) 1 calc R U P A 2
C46B C 0.6641(15) 0.294(2) 1.1580(10) 0.135(3) Uani 0.256(8) 1 d D U P A 2
H46A H 0.7095 0.3296 1.1598 0.203 Uiso 0.256(8) 1 calc R U P A 2
H46B H 0.6682 0.2105 1.1544 0.203 Uiso 0.256(8) 1 calc R U P A 2
H46C H 0.6517 0.3111 1.1932 0.203 Uiso 0.256(8) 1 calc R U P A 2
O8A O 0.6485(4) 0.4337(4) 1.1176(3) 0.0817(19) Uani 0.744(8) 1 d D U P A 1
C45A C 0.6228(5) 0.3291(5) 1.1365(4) 0.114(3) Uani 0.744(8) 1 d D U P A 1
H45C H 0.5708 0.3229 1.1193 0.136 Uiso 0.744(8) 1 calc R U P A 1
H45D H 0.6335 0.3290 1.1789 0.136 Uiso 0.744(8) 1 calc R U P A 1
C46A C 0.6601(5) 0.2281(6) 1.1171(4) 0.135(3) Uani 0.744(8) 1 d D U P A 1
H46D H 0.6450 0.2240 1.0750 0.203 Uiso 0.744(8) 1 calc R U P A 1
H46E H 0.6475 0.1569 1.1329 0.203 Uiso 0.744(8) 1 calc R U P A 1
H46F H 0.7116 0.2392 1.1311 0.203 Uiso 0.744(8) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O1 1.916(2) . ?
Fe1 O2 1.940(2) . ?
Fe1 N3 2.077(3) . ?
Fe1 N4 2.080(3) . ?
Fe1 N1 2.084(3) . ?
Fe1 N2 2.194(3) . ?
Fe2 O3 1.916(2) . ?
Fe2 O4 1.940(2) . ?
Fe2 N8 2.069(3) . ?
Fe2 N7 2.082(3) . ?
Fe2 N5 2.087(3) . ?
Fe2 N6 2.201(3) . ?
S1 C47 1.615(4) . ?
S2 C48 1.611(4) . ?
O1 C1 1.318(3) . ?
O2 C19 1.316(3) . ?
O3 C20 1.319(4) . ?
O4 C38 1.314(4) . ?
O5 C2 1.363(4) . ?
O5 C39 1.439(4) . ?
O6 C18 1.382(4) . ?
O6 C41 1.450(4) . ?
O7 C37 1.383(4) . ?
O7 C43 1.459(4) . ?
N1 C7 1.278(4) . ?
N1 C8 1.461(4) . ?
N2 C10 1.475(4) . ?
N2 C9 1.483(4) . ?
N3 C13 1.286(4) . ?
N3 C12 1.476(4) . ?
N4 C47 1.148(4) . ?
N5 C26 1.276(4) . ?
N5 C27 1.462(4) . ?
N6 C29 1.478(5) . ?
N6 C28 1.481(5) . ?
N7 C32 1.288(4) . ?
N7 C31 1.472(4) . ?
N8 C48 1.148(4) . ?
C1 C6 1.406(4) . ?
C1 C2 1.413(4) . ?
C2 C3 1.377(5) . ?
C3 C4 1.374(5) . ?
C4 C5 1.356(5) . ?
C5 C6 1.413(5) . ?
C6 C7 1.439(5) . ?
C8 C9 1.504(5) . ?
C10 C11 1.509(5) . ?
C11 C12 1.531(5) . ?
C13 C14 1.450(5) . ?
C14 C15 1.401(4) . ?
C14 C19 1.406(4) . ?
C15 C16 1.365(5) . ?
C16 C17 1.383(5) . ?
C17 C18 1.376(4) . ?
C18 C19 1.413(4) . ?
C20 C25 1.406(5) . ?
C20 C21 1.424(5) . ?
C21 O8B 1.366(10) . ?
C21 O8A 1.366(5) . ?
C21 C22 1.380(5) . ?
C22 C23 1.365(6) . ?
C23 C24 1.363(6) . ?
C24 C25 1.408(5) . ?
C25 C26 1.433(5) . ?
C27 C28 1.504(5) . ?
C29 C30 1.509(5) . ?
C30 C31 1.527(5) . ?
C32 C33 1.436(5) . ?
C33 C34 1.401(4) . ?
C33 C38 1.408(4) . ?
C34 C35 1.355(5) . ?
C35 C36 1.382(5) . ?
C36 C37 1.379(5) . ?
C37 C38 1.408(4) . ?
C39 C40 1.469(7) . ?
C41 C42 1.478(5) . ?
C43 C44 1.464(6) . ?
O8B C45B 1.438(9) . ?
C45B C46B 1.537(10) . ?
O8A C45A 1.420(6) . ?
C45A C46A 1.506(7) . ?

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 94.66(9) . . ?
O1 Fe1 N3 105.98(10) . . ?
O2 Fe1 N3 84.70(10) . . ?
O1 Fe1 N4 90.15(10) . . ?
O2 Fe1 N4 175.11(10) . . ?
N3 Fe1 N4 93.15(11) . . ?
O1 Fe1 N1 88.54(10) . . ?
O2 Fe1 N1 90.95(9) . . ?
N3 Fe1 N1 165.10(11) . . ?
N4 Fe1 N1 90.04(11) . . ?
O1 Fe1 N2 167.04(10) . . ?
O2 Fe1 N2 89.44(10) . . ?
N3 Fe1 N2 86.62(11) . . ?
N4 Fe1 N2 86.05(11) . . ?
N1 Fe1 N2 79.08(11) . . ?
O3 Fe2 O4 94.94(10) . . ?
O3 Fe2 N8 89.01(11) . . ?
O4 Fe2 N8 175.98(11) . . ?
O3 Fe2 N7 107.37(10) . . ?
O4 Fe2 N7 84.82(10) . . ?
N8 Fe2 N7 93.31(12) . . ?
O3 Fe2 N5 88.67(11) . . ?
O4 Fe2 N5 87.97(10) . . ?
N8 Fe2 N5 92.86(12) . . ?
N7 Fe2 N5 162.90(11) . . ?
O3 Fe2 N6 166.54(11) . . ?
O4 Fe2 N6 90.53(10) . . ?
N8 Fe2 N6 85.76(11) . . ?
N7 Fe2 N6 85.33(11) . . ?
N5 Fe2 N6 79.23(12) . . ?
C1 O1 Fe1 128.2(2) . . ?
C19 O2 Fe1 121.10(18) . . ?
C20 O3 Fe2 129.9(2) . . ?
C38 O4 Fe2 123.64(19) . . ?
C2 O5 C39 118.7(3) . . ?
C18 O6 C41 115.4(2) . . ?
C37 O7 C43 113.1(3) . . ?
C7 N1 C8 121.8(3) . . ?
C7 N1 Fe1 124.2(2) . . ?
C8 N1 Fe1 113.5(2) . . ?
C10 N2 C9 111.1(3) . . ?
C10 N2 Fe1 117.2(2) . . ?
C9 N2 Fe1 107.9(2) . . ?
C13 N3 C12 119.1(3) . . ?
C13 N3 Fe1 122.3(2) . . ?
C12 N3 Fe1 118.5(2) . . ?
C47 N4 Fe1 172.9(3) . . ?
C26 N5 C27 121.5(3) . . ?
C26 N5 Fe2 125.3(3) . . ?
C27 N5 Fe2 113.2(2) . . ?
C29 N6 C28 111.9(3) . . ?
C29 N6 Fe2 117.3(2) . . ?
C28 N6 Fe2 107.3(2) . . ?
C32 N7 C31 118.4(3) . . ?
C32 N7 Fe2 122.5(2) . . ?
C31 N7 Fe2 118.9(2) . . ?
C48 N8 Fe2 169.2(3) . . ?
O1 C1 C6 123.3(3) . . ?
O1 C1 C2 118.6(3) . . ?
C6 C1 C2 118.1(3) . . ?
O5 C2 C3 124.3(3) . . ?
O5 C2 C1 115.3(3) . . ?
C3 C2 C1 120.3(3) . . ?
C4 C3 C2 121.1(4) . . ?
C5 C4 C3 120.1(4) . . ?
C4 C5 C6 120.9(4) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C7 123.6(3) . . ?
C5 C6 C7 117.0(3) . . ?
N1 C7 C6 125.6(3) . . ?
N1 C8 C9 106.7(3) . . ?
N2 C9 C8 109.2(3) . . ?
N2 C10 C11 114.0(3) . . ?
C10 C11 C12 117.2(3) . . ?
N3 C12 C11 109.2(3) . . ?
N3 C13 C14 124.7(3) . . ?
C15 C14 C19 120.1(3) . . ?
C15 C14 C13 118.8(3) . . ?
C19 C14 C13 120.7(3) . . ?
C16 C15 C14 120.7(3) . . ?
C15 C16 C17 119.9(3) . . ?
C18 C17 C16 120.8(3) . . ?
C17 C18 O6 119.4(3) . . ?
C17 C18 C19 120.6(3) . . ?
O6 C18 C19 119.9(3) . . ?
O2 C19 C14 122.7(3) . . ?
O2 C19 C18 119.5(3) . . ?
C14 C19 C18 117.8(3) . . ?
O3 C20 C25 123.8(3) . . ?
O3 C20 C21 118.4(3) . . ?
C25 C20 C21 117.7(3) . . ?
O8B C21 C22 126.8(10) . . ?
O8A C21 C22 123.0(4) . . ?
O8B C21 C20 110.6(9) . . ?
O8A C21 C20 116.4(4) . . ?
C22 C21 C20 120.1(4) . . ?
C23 C22 C21 121.3(4) . . ?
C24 C23 C22 120.3(4) . . ?
C23 C24 C25 120.7(4) . . ?
C20 C25 C24 119.8(4) . . ?
C20 C25 C26 123.0(3) . . ?
C24 C25 C26 117.2(4) . . ?
N5 C26 C25 126.3(3) . . ?
N5 C27 C28 107.0(3) . . ?
N6 C28 C27 109.1(3) . . ?
N6 C29 C30 113.9(3) . . ?
C29 C30 C31 116.1(3) . . ?
N7 C31 C30 109.7(3) . . ?
N7 C32 C33 125.7(3) . . ?
C34 C33 C38 119.8(3) . . ?
C34 C33 C32 119.2(3) . . ?
C38 C33 C32 120.7(3) . . ?
C35 C34 C33 121.4(4) . . ?
C34 C35 C36 119.7(4) . . ?
C37 C36 C35 120.5(4) . . ?
C36 C37 O7 119.6(3) . . ?
C36 C37 C38 121.1(3) . . ?
O7 C37 C38 119.3(3) . . ?
O4 C38 C37 119.6(3) . . ?
O4 C38 C33 122.9(3) . . ?
C37 C38 C33 117.4(3) . . ?
O5 C39 C40 112.4(4) . . ?
O6 C41 C42 109.2(3) . . ?
O7 C43 C44 108.0(4) . . ?
N4 C47 S1 178.3(3) . . ?
N8 C48 S2 178.6(4) . . ?
C21 O8B C45B 120.3(13) . . ?
O8B C45B C46B 102.3(12) . . ?
C21 O8A C45A 118.8(5) . . ?
O8A C45A C46A 107.9(6) . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.054

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 995957'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2@100K

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis((2-oxido-1-naphthyl)methylene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Fe N4 O2 S'
_chemical_formula_weight         537.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3460 0.8440 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.5011(6)
_cell_length_b                   13.0676(10)
_cell_length_c                   24.704(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2421.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4554
_cell_measurement_theta_min      2.9264
_cell_measurement_theta_max      33.2245

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.744
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8399
_diffrn_reflns_av_unetI/netI     0.1045
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.924
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             4168
_reflns_number_gt                3084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.942

_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       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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     
'w=1/[σ²(Fo²)+(0.0407P)²] 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_abs_structure_details 
;
 Flack x determined using 1057 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4168
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0857
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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
C1 C 0.0208(9) 1.0778(4) 0.1335(2) 0.0146(13) Uani 1 1 d . . . . .
C2 C -0.0523(8) 1.1421(4) 0.0925(2) 0.0185(16) Uani 1 1 d . . . . .
H2 H -0.1706 1.1303 0.0802 0.022 Uiso 1 1 calc R U . . .
C3 C 0.0430(9) 1.2194(5) 0.0706(2) 0.0202(16) Uani 1 1 d . . . . .
H3 H -0.0109 1.2607 0.0435 0.024 Uiso 1 1 calc R U . . .
C4 C 0.2194(9) 1.2413(5) 0.0866(3) 0.0199(16) Uani 1 1 d . . . . .
C5 C 0.3144(11) 1.3229(5) 0.0638(3) 0.0293(18) Uani 1 1 d . . . . .
H5 H 0.2602 1.3641 0.0367 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4859(12) 1.3440(5) 0.0803(3) 0.0321(18) Uani 1 1 d . . . . .
H6 H 0.5506 1.3993 0.0649 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5632(9) 1.2821(5) 0.1203(3) 0.0283(18) Uani 1 1 d . . . . .
H7 H 0.6818 1.2958 0.1316 0.034 Uiso 1 1 calc R U . . .
C8 C 0.4735(9) 1.2037(5) 0.1432(2) 0.0197(15) Uani 1 1 d . . . . .
H8 H 0.5303 1.1631 0.1701 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2972(9) 1.1813(5) 0.1279(2) 0.0181(15) Uani 1 1 d . . . . .
C10 C 0.1943(7) 1.0999(5) 0.1519(2) 0.0138(13) Uani 1 1 d . . . . .
C11 C 0.2519(8) 1.0523(4) 0.2019(2) 0.0132(14) Uani 1 1 d . . . . .
H11 H 0.3463 1.0847 0.2209 0.016 Uiso 1 1 calc R U . . .
C12 C 0.2261(8) 0.9489(5) 0.2797(2) 0.0200(15) Uani 1 1 d . . . . .
H12A H 0.3225 0.9946 0.2926 0.024 Uiso 1 1 calc R U . . .
H12B H 0.2682 0.8774 0.2831 0.024 Uiso 1 1 calc R U . . .
C13 C 0.0621(7) 0.9638(5) 0.3147(3) 0.0202(15) Uani 1 1 d . . . . .
H13A H 0.0968 0.9544 0.3531 0.024 Uiso 1 1 calc R U . . .
H13B H 0.0205 1.0352 0.3105 0.024 Uiso 1 1 calc R U . . .
C14 C -0.0920(7) 0.8928(5) 0.3025(2) 0.0181(14) Uani 1 1 d . . . . .
H14A H -0.0528 0.8212 0.3078 0.022 Uiso 1 1 calc R U . . .
H14B H -0.1899 0.9065 0.3284 0.022 Uiso 1 1 calc R U . . .
C15 C -0.3166(9) 0.8380(5) 0.2365(2) 0.0203(15) Uani 1 1 d . . . . .
H15A H -0.4229 0.8654 0.2554 0.024 Uiso 1 1 calc R U . . .
H15B H -0.2929 0.7681 0.2503 0.024 Uiso 1 1 calc R U . . .
C16 C -0.3490(8) 0.8351(5) 0.1762(2) 0.0174(15) Uani 1 1 d . . . . .
H16A H -0.4373 0.7815 0.1670 0.021 Uiso 1 1 calc R U . . .
H16B H -0.3940 0.9019 0.1632 0.021 Uiso 1 1 calc R U . . .
C17 C -0.1595(8) 0.7452(4) 0.1138(2) 0.0127(14) Uani 1 1 d . . . . .
H17 H -0.2635 0.7100 0.1022 0.015 Uiso 1 1 calc R U . . .
C18 C 0.0043(9) 0.7208(4) 0.0879(2) 0.0137(13) Uani 1 1 d . . . . .
C19 C 0.0114(9) 0.6370(4) 0.0495(2) 0.0174(14) Uani 1 1 d . . . . .
C20 C -0.1356(9) 0.5716(5) 0.0391(3) 0.0194(15) Uani 1 1 d . . . . .
H20 H -0.2412 0.5782 0.0600 0.023 Uiso 1 1 calc R U . . .
C21 C -0.1269(9) 0.4985(5) -0.0012(3) 0.0236(16) Uani 1 1 d . . . . .
H21 H -0.2272 0.4559 -0.0078 0.028 Uiso 1 1 calc R U . . .
C22 C 0.0264(9) 0.4863(5) -0.0321(3) 0.0250(16) Uani 1 1 d . . . . .
H22 H 0.0303 0.4366 -0.0601 0.030 Uiso 1 1 calc R U . . .
C23 C 0.1706(9) 0.5460(5) -0.0219(3) 0.0211(16) Uani 1 1 d . . . . .
H23 H 0.2758 0.5369 -0.0428 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1676(8) 0.6213(5) 0.0189(2) 0.0170(14) Uani 1 1 d . . . . .
C25 C 0.3188(9) 0.6838(5) 0.0286(2) 0.0185(15) Uani 1 1 d . . . . .
H25 H 0.4260 0.6711 0.0093 0.022 Uiso 1 1 calc R U . . .
C26 C 0.3131(8) 0.7612(5) 0.0649(2) 0.0159(14) Uani 1 1 d . . . . .
H26 H 0.4163 0.8021 0.0701 0.019 Uiso 1 1 calc R U . . .
C27 C 0.1563(8) 0.7833(5) 0.0955(2) 0.0149(14) Uani 1 1 d . . . . .
C28 C 0.2108(9) 0.6982(5) 0.2159(3) 0.0220(16) Uani 1 1 d . . . . .
Fe1 Fe 0.01101(12) 0.88723(6) 0.18570(3) 0.0136(2) Uani 1 1 d . . . . .
N1 N -0.1768(7) 0.8119(4) 0.1519(2) 0.0140(12) Uani 1 1 d . . . . .
N2 N -0.1599(7) 0.9051(4) 0.24668(18) 0.0182(13) Uani 1 1 d . . . . .
H1N2 H -0.2046 0.9770 0.2441 0.022 Uiso 1 1 calc R U . . .
N3 N 0.1879(6) 0.9712(4) 0.22271(19) 0.0136(12) Uani 1 1 d . . . . .
N4 N 0.1071(7) 0.7610(4) 0.2190(2) 0.0179(12) Uani 1 1 d . . . . .
O1 O 0.1679(5) 0.8617(3) 0.12745(15) 0.0162(10) Uani 1 1 d . . . . .
O2 O -0.0803(5) 1.0061(3) 0.15294(17) 0.0167(10) Uani 1 1 d . . . . .
S1 S 0.3661(2) 0.61054(14) 0.21104(7) 0.0271(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.297(7) . ?
C1 C10 1.409(8) . ?
C1 C2 1.427(8) . ?
C2 C3 1.350(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.410(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(9) . ?
C4 C9 1.413(9) . ?
C5 C6 1.377(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.350(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.442(8) . ?
C10 C11 1.448(8) . ?
C11 N3 1.272(7) . ?
C11 H11 0.9500 . ?
C12 N3 1.465(8) . ?
C12 C13 1.517(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.512(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.479(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 N2 1.488(8) . ?
C15 C16 1.512(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N1 1.456(7) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N1 1.290(7) . ?
C17 C18 1.422(9) . ?
C17 H17 0.9500 . ?
C18 C27 1.415(9) . ?
C18 C19 1.450(7) . ?
C19 C24 1.409(8) . ?
C19 C20 1.419(9) . ?
C20 C21 1.381(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.357(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.409(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.418(9) . ?
C25 C26 1.351(8) . ?
C25 H25 0.9500 . ?
C26 C27 1.428(8) . ?
C26 H26 0.9500 . ?
C27 O1 1.295(7) . ?
C28 N4 1.133(8) . ?
C28 S1 1.638(8) . ?
Fe1 O2 1.881(4) . ?
Fe1 O1 1.889(4) . ?
Fe1 N1 1.910(5) . ?
Fe1 N3 1.950(5) . ?
Fe1 N4 1.979(6) . ?
Fe1 N2 1.992(5) . ?
N2 H1N2 1.0000 . ?

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 C1 C10 124.6(5) . . ?
O2 C1 C2 117.6(6) . . ?
C10 C1 C2 117.6(5) . . ?
C3 C2 C1 121.4(6) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 122.5(6) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 121.3(6) . . ?
C5 C4 C9 120.2(6) . . ?
C3 C4 C9 118.5(6) . . ?
C6 C5 C4 120.5(7) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 118.6(6) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 121.8(7) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 120.9(6) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 117.9(6) . . ?
C8 C9 C10 123.1(6) . . ?
C4 C9 C10 119.1(6) . . ?
C1 C10 C9 120.8(5) . . ?
C1 C10 C11 117.6(5) . . ?
C9 C10 C11 120.5(5) . . ?
N3 C11 C10 126.1(5) . . ?
N3 C11 H11 116.9 . . ?
C10 C11 H11 116.9 . . ?
N3 C12 C13 111.3(5) . . ?
N3 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 115.3(5) . . ?
C14 C13 H13A 108.5 . . ?
C12 C13 H13A 108.5 . . ?
C14 C13 H13B 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
N2 C14 C13 112.5(5) . . ?
N2 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
N2 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N2 C15 C16 108.0(5) . . ?
N2 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
N2 C15 H15B 110.1 . . ?
C16 C15 H15B 110.1 . . ?
H15A C15 H15B 108.4 . . ?
N1 C16 C15 105.6(5) . . ?
N1 C16 H16A 110.6 . . ?
C15 C16 H16A 110.6 . . ?
N1 C16 H16B 110.6 . . ?
C15 C16 H16B 110.6 . . ?
H16A C16 H16B 108.8 . . ?
N1 C17 C18 124.6(6) . . ?
N1 C17 H17 117.7 . . ?
C18 C17 H17 117.7 . . ?
C27 C18 C17 120.4(5) . . ?
C27 C18 C19 119.6(6) . . ?
C17 C18 C19 119.7(6) . . ?
C24 C19 C20 117.5(5) . . ?
C24 C19 C18 119.4(6) . . ?
C20 C19 C18 123.0(6) . . ?
C21 C20 C19 120.7(6) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.9(6) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 119.5(6) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 121.4(6) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 119.9(6) . . ?
C23 C24 C25 120.7(6) . . ?
C19 C24 C25 119.3(6) . . ?
C26 C25 C24 121.2(6) . . ?
C26 C25 H25 119.4 . . ?
C24 C25 H25 119.4 . . ?
C25 C26 C27 121.9(6) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
O1 C27 C18 126.3(5) . . ?
O1 C27 C26 115.3(6) . . ?
C18 C27 C26 118.4(6) . . ?
N4 C28 S1 177.9(6) . . ?
O2 Fe1 O1 92.58(18) . . ?
O2 Fe1 N1 88.2(2) . . ?
O1 Fe1 N1 92.04(19) . . ?
O2 Fe1 N3 89.10(19) . . ?
O1 Fe1 N3 91.89(19) . . ?
N1 Fe1 N3 175.3(2) . . ?
O2 Fe1 N4 179.0(2) . . ?
O1 Fe1 N4 86.7(2) . . ?
N1 Fe1 N4 91.2(2) . . ?
N3 Fe1 N4 91.5(2) . . ?
O2 Fe1 N2 89.68(19) . . ?
O1 Fe1 N2 176.4(2) . . ?
N1 Fe1 N2 85.2(2) . . ?
N3 Fe1 N2 91.0(2) . . ?
N4 Fe1 N2 91.0(2) . . ?
C17 N1 C16 122.0(5) . . ?
C17 N1 Fe1 126.4(4) . . ?
C16 N1 Fe1 111.6(4) . . ?
C14 N2 C15 111.4(5) . . ?
C14 N2 Fe1 118.1(4) . . ?
C15 N2 Fe1 108.2(4) . . ?
C14 N2 H1N2 106.1 . . ?
C15 N2 H1N2 106.1 . . ?
Fe1 N2 H1N2 106.1 . . ?
C11 N3 C12 118.7(5) . . ?
C11 N3 Fe1 122.4(4) . . ?
C12 N3 Fe1 118.1(4) . . ?
C28 N4 Fe1 145.7(5) . . ?
C27 O1 Fe1 124.2(4) . . ?
C1 O2 Fe1 122.9(4) . . ?

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.082

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 995958'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2@298K

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis((2-oxido-1-naphthyl)methylene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Fe N4 O2 S'
_chemical_formula_weight         537.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3460 0.8440 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   7.5422(3)
_cell_length_b                   13.5725(5)
_cell_length_c                   24.6626(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2524.62(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4836
_cell_measurement_theta_min      2.9248
_cell_measurement_theta_max      33.2288

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.713
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20049
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.897
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4438
_reflns_number_gt                3328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.975

_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       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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     
'w=1/[σ²(Fo²)+(0.0329P)²] 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_abs_structure_details 
;
 Flack x determined using 1175 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4438
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0606
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_restrained_S_all      0.897
_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
C1 C 0.0402(5) 1.0897(2) 0.13040(12) 0.0427(9) Uani 1 1 d . . . . .
C2 C -0.0235(7) 1.1527(3) 0.08835(14) 0.0571(11) Uani 1 1 d . . . . .
H2 H -0.1353 1.1417 0.0736 0.069 Uiso 1 1 calc R U . . .
C3 C 0.0755(8) 1.2272(3) 0.06976(15) 0.0682(14) Uani 1 1 d . . . . .
H3 H 0.0291 1.2676 0.0428 0.082 Uiso 1 1 calc R U . . .
C4 C 0.2465(8) 1.2466(3) 0.08940(16) 0.0606(12) Uani 1 1 d . . . . .
C5 C 0.3522(10) 1.3244(4) 0.06892(18) 0.096(2) Uani 1 1 d . . . . .
H5 H 0.3069 1.3653 0.0420 0.115 Uiso 1 1 calc R U . . .
C6 C 0.5177(12) 1.3400(4) 0.0879(2) 0.115(2) Uani 1 1 d . . . . .
H6 H 0.5851 1.3914 0.0739 0.138 Uiso 1 1 calc R U . . .
C7 C 0.5880(8) 1.2805(4) 0.1277(2) 0.0944(19) Uani 1 1 d . . . . .
H7 H 0.7027 1.2916 0.1401 0.113 Uiso 1 1 calc R U . . .
C8 C 0.4891(6) 1.2046(3) 0.14935(16) 0.0652(12) Uani 1 1 d . . . . .
H8 H 0.5385 1.1644 0.1759 0.078 Uiso 1 1 calc R U . . .
C9 C 0.3149(6) 1.1871(3) 0.13177(15) 0.0505(11) Uani 1 1 d . . . . .
C10 C 0.2057(5) 1.1095(3) 0.15352(13) 0.0394(8) Uani 1 1 d . . . . .
C11 C 0.2527(5) 1.0642(3) 0.20383(14) 0.0434(10) Uani 1 1 d . . . . .
H11 H 0.3395 1.0954 0.2244 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2185(5) 0.9608(3) 0.28069(14) 0.0531(10) Uani 1 1 d . . . . .
H12A H 0.3065 1.0055 0.2955 0.064 Uiso 1 1 calc R U . . .
H12B H 0.2644 0.8942 0.2836 0.064 Uiso 1 1 calc R U . . .
C13 C 0.0475(5) 0.9694(3) 0.31305(13) 0.0546(10) Uani 1 1 d . . . . .
H13A H 0.0762 0.9622 0.3512 0.065 Uiso 1 1 calc R U . . .
H13B H 0.0007 1.0353 0.3080 0.065 Uiso 1 1 calc R U . . .
C14 C -0.0975(5) 0.8965(3) 0.29935(13) 0.0528(10) Uani 1 1 d . . . . .
H14A H -0.0518 0.8302 0.3039 0.063 Uiso 1 1 calc R U . . .
H14B H -0.1946 0.9049 0.3247 0.063 Uiso 1 1 calc R U . . .
C15 C -0.3165(5) 0.8415(3) 0.23209(15) 0.0563(11) Uani 1 1 d . . . . .
H15A H -0.4216 0.8654 0.2506 0.068 Uiso 1 1 calc R U . . .
H15B H -0.2904 0.7759 0.2455 0.068 Uiso 1 1 calc R U . . .
C16 C -0.3505(5) 0.8376(3) 0.17143(15) 0.0553(10) Uani 1 1 d . . . . .
H16A H -0.4371 0.7870 0.1630 0.066 Uiso 1 1 calc R U . . .
H16B H -0.3952 0.9004 0.1586 0.066 Uiso 1 1 calc R U . . .
C17 C -0.1666(5) 0.7452(3) 0.11093(14) 0.0457(10) Uani 1 1 d . . . . .
H17 H -0.2682 0.7096 0.1024 0.055 Uiso 1 1 calc R U . . .
C18 C -0.0062(5) 0.7175(2) 0.08403(12) 0.0409(9) Uani 1 1 d . . . . .
C19 C -0.0057(6) 0.6325(2) 0.04787(12) 0.0470(9) Uani 1 1 d . . . . .
C20 C -0.1532(6) 0.5720(3) 0.03896(16) 0.0627(12) Uani 1 1 d . . . . .
H20 H -0.2562 0.5825 0.0589 0.075 Uiso 1 1 calc R U . . .
C21 C -0.1485(8) 0.4970(3) 0.00105(19) 0.0787(15) Uani 1 1 d . . . . .
H21 H -0.2483 0.4579 -0.0043 0.094 Uiso 1 1 calc R U . . .
C22 C 0.0023(9) 0.4794(3) -0.02892(19) 0.0876(15) Uani 1 1 d . . . . .
H22 H 0.0032 0.4299 -0.0550 0.105 Uiso 1 1 calc R U . . .
C23 C 0.1495(7) 0.5345(3) -0.02027(17) 0.0729(14) Uani 1 1 d . . . . .
H23 H 0.2518 0.5211 -0.0400 0.087 Uiso 1 1 calc R U . . .
C24 C 0.1506(6) 0.6115(3) 0.01796(13) 0.0517(10) Uani 1 1 d . . . . .
C25 C 0.3031(6) 0.6700(3) 0.02557(15) 0.0574(11) Uani 1 1 d . . . . .
H25 H 0.4073 0.6533 0.0076 0.069 Uiso 1 1 calc R U . . .
C26 C 0.3012(6) 0.7494(3) 0.05813(14) 0.0509(10) Uani 1 1 d . . . . .
H26 H 0.4028 0.7877 0.0614 0.061 Uiso 1 1 calc R U . . .
C27 C 0.1467(5) 0.7755(3) 0.08752(13) 0.0422(10) Uani 1 1 d . . . . .
C28 C 0.2262(6) 0.7056(3) 0.21244(15) 0.0499(10) Uani 1 1 d . . . . .
Fe1 Fe 0.02427(6) 0.89506(3) 0.17805(2) 0.04023(15) Uani 1 1 d . . . . .
N1 N -0.1831(4) 0.8153(2) 0.14609(12) 0.0434(8) Uani 1 1 d . . . . .
N2 N -0.1664(4) 0.9073(2) 0.24342(10) 0.0424(7) Uani 1 1 d . . . . .
H1N2 H -0.2139 0.9744 0.2412 0.051 Uiso 1 1 calc R U . . .
N3 N 0.1870(4) 0.9846(2) 0.22335(11) 0.0417(7) Uani 1 1 d . . . . .
N4 N 0.1288(5) 0.7687(2) 0.21792(13) 0.0547(9) Uani 1 1 d . . . . .
O1 O 0.1560(3) 0.85796(17) 0.11556(10) 0.0492(7) Uani 1 1 d . . . . .
O2 O -0.0633(3) 1.01821(17) 0.14676(10) 0.0474(7) Uani 1 1 d . . . . .
S1 S 0.36636(14) 0.61418(8) 0.20414(5) 0.0727(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.309(4) . ?
C1 C10 1.398(5) . ?
C1 C2 1.427(5) . ?
C2 C3 1.338(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.416(7) . ?
C4 C9 1.417(6) . ?
C5 C6 1.349(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.441(5) . ?
C10 C11 1.430(5) . ?
C11 N3 1.282(4) . ?
C11 H11 0.9300 . ?
C12 N3 1.470(4) . ?
C12 C13 1.521(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.513(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.481(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N2 1.469(5) . ?
C15 C16 1.519(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N1 1.441(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N1 1.293(4) . ?
C17 C18 1.430(5) . ?
C17 H17 0.9300 . ?
C18 C27 1.399(5) . ?
C18 C19 1.459(4) . ?
C19 C20 1.400(5) . ?
C19 C24 1.419(5) . ?
C20 C21 1.383(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.355(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.408(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.410(6) . ?
C25 C26 1.344(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.418(5) . ?
C26 H26 0.9300 . ?
C27 O1 1.317(4) . ?
C28 N4 1.136(5) . ?
C28 S1 1.643(5) . ?
Fe1 O1 1.902(2) . ?
Fe1 O2 1.956(2) . ?
Fe1 N3 2.057(3) . ?
Fe1 N1 2.059(3) . ?
Fe1 N4 2.129(4) . ?
Fe1 N2 2.167(3) . ?
N2 H1N2 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 C1 C10 123.3(3) . . ?
O2 C1 C2 117.9(4) . . ?
C10 C1 C2 118.8(3) . . ?
C3 C2 C1 120.9(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 122.4(4) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 122.3(5) . . ?
C3 C4 C9 118.8(4) . . ?
C5 C4 C9 118.9(5) . . ?
C6 C5 C4 120.9(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.7(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 120.4(6) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 118.2(4) . . ?
C8 C9 C10 122.9(4) . . ?
C4 C9 C10 118.9(4) . . ?
C1 C10 C11 119.5(3) . . ?
C1 C10 C9 119.9(3) . . ?
C11 C10 C9 119.7(3) . . ?
N3 C11 C10 126.3(3) . . ?
N3 C11 H11 116.8 . . ?
C10 C11 H11 116.8 . . ?
N3 C12 C13 110.5(3) . . ?
N3 C12 H12A 109.5 . . ?
C13 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
C13 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C12 116.5(3) . . ?
C14 C13 H13A 108.2 . . ?
C12 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
N2 C14 C13 113.3(3) . . ?
N2 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
N2 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
N2 C15 C16 109.8(3) . . ?
N2 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N1 C16 C15 106.6(3) . . ?
N1 C16 H16A 110.4 . . ?
C15 C16 H16A 110.4 . . ?
N1 C16 H16B 110.4 . . ?
C15 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
N1 C17 C18 125.8(3) . . ?
N1 C17 H17 117.1 . . ?
C18 C17 H17 117.1 . . ?
C27 C18 C17 121.4(3) . . ?
C27 C18 C19 118.7(4) . . ?
C17 C18 C19 119.6(4) . . ?
C20 C19 C24 117.5(3) . . ?
C20 C19 C18 123.9(4) . . ?
C24 C19 C18 118.6(4) . . ?
C21 C20 C19 121.2(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 120.7(5) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 121.3(4) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C25 120.8(4) . . ?
C23 C24 C19 119.5(4) . . ?
C25 C24 C19 119.7(4) . . ?
C26 C25 C24 121.5(4) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
O1 C27 C18 123.7(3) . . ?
O1 C27 C26 115.9(3) . . ?
C18 C27 C26 120.4(3) . . ?
N4 C28 S1 179.6(4) . . ?
O1 Fe1 O2 94.76(10) . . ?
O1 Fe1 N3 106.55(11) . . ?
O2 Fe1 N3 84.87(10) . . ?
O1 Fe1 N1 86.98(11) . . ?
O2 Fe1 N1 92.42(11) . . ?
N3 Fe1 N1 166.36(12) . . ?
O1 Fe1 N4 88.13(12) . . ?
O2 Fe1 N4 174.87(11) . . ?
N3 Fe1 N4 90.24(12) . . ?
N1 Fe1 N4 91.97(12) . . ?
O1 Fe1 N2 165.98(10) . . ?
O2 Fe1 N2 90.22(11) . . ?
N3 Fe1 N2 86.92(11) . . ?
N1 Fe1 N2 79.71(11) . . ?
N4 Fe1 N2 87.94(12) . . ?
C17 N1 C16 122.0(3) . . ?
C17 N1 Fe1 124.8(3) . . ?
C16 N1 Fe1 112.9(2) . . ?
C15 N2 C14 112.7(3) . . ?
C15 N2 Fe1 108.8(2) . . ?
C14 N2 Fe1 116.9(2) . . ?
C15 N2 H1N2 105.8 . . ?
C14 N2 H1N2 105.8 . . ?
Fe1 N2 H1N2 105.8 . . ?
C11 N3 C12 118.9(3) . . ?
C11 N3 Fe1 121.6(2) . . ?
C12 N3 Fe1 119.3(2) . . ?
C28 N4 Fe1 142.4(3) . . ?
C27 O1 Fe1 128.5(2) . . ?
C1 O2 Fe1 123.7(2) . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 995959'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis(5-nitro-2-oxido-benzylidene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H19 Fe N6 O6 S'
_chemical_formula_weight         527.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3460 0.8440 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   15.9030(5)
_cell_length_b                   14.2180(5)
_cell_length_c                   19.6342(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4439.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17074
_cell_measurement_theta_min      2.9234
_cell_measurement_theta_max      33.2587

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2168
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7501
_exptl_absorpt_correction_T_max  0.8794
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.3611
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40122
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3907
_reflns_number_gt                3038
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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)+(0.0443P)²+3.5325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3907
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.0866(2) -0.0260(2) 0.17715(16) 0.0397(8) Uani 1 1 d . . .
H12A H 0.0391 -0.0536 0.1514 0.048 Uiso 1 1 calc R . .
H12B H 0.0748 -0.0329 0.2264 0.048 Uiso 1 1 calc R . .
O4 O 0.09020(14) 0.46075(15) 0.53925(11) 0.0455(6) Uani 1 1 d . . .
O6 O 0.03204(17) 0.3681(2) -0.12784(12) 0.0693(9) Uani 1 1 d . . .
C1 C 0.12600(16) 0.30182(18) 0.31714(13) 0.0229(6) Uani 1 1 d . . .
C2 C 0.05841(18) 0.34984(19) 0.34829(14) 0.0281(6) Uani 1 1 d . . .
H2 H 0.0061 0.3541 0.3251 0.034 Uiso 1 1 calc R . .
C3 C 0.06678(18) 0.39031(19) 0.41117(14) 0.0299(7) Uani 1 1 d . . .
H3 H 0.0206 0.4221 0.4315 0.036 Uiso 1 1 calc R . .
C4 C 0.14308(18) 0.38454(19) 0.44500(13) 0.0268(6) Uani 1 1 d . . .
C5 C 0.21155(18) 0.34209(19) 0.41581(13) 0.0261(6) Uani 1 1 d . . .
H5 H 0.2638 0.3409 0.4393 0.031 Uiso 1 1 calc R . .
C6 C 0.20465(17) 0.30060(19) 0.35164(13) 0.0242(6) Uani 1 1 d . . .
C7 C 0.28013(17) 0.26037(19) 0.32213(13) 0.0260(6) Uani 1 1 d . . .
H7 H 0.3321 0.2723 0.3444 0.031 Uiso 1 1 calc R . .
C8 C 0.35962(18) 0.1711(2) 0.24143(14) 0.0323(7) Uani 1 1 d . . .
H8A H 0.4069 0.1850 0.2727 0.039 Uiso 1 1 calc R . .
H8B H 0.3724 0.1988 0.1964 0.039 Uiso 1 1 calc R . .
C9 C 0.34729(19) 0.0662(2) 0.23510(15) 0.0370(8) Uani 1 1 d . . .
H9A H 0.3960 0.0378 0.2115 0.044 Uiso 1 1 calc R . .
H9B H 0.3427 0.0376 0.2809 0.044 Uiso 1 1 calc R . .
C10 C 0.2432(2) -0.0515(2) 0.20154(15) 0.0416(8) Uani 1 1 d . . .
H10A H 0.2307 -0.0656 0.2499 0.050 Uiso 1 1 calc R . .
H10B H 0.2907 -0.0921 0.1875 0.050 Uiso 1 1 calc R . .
C11 C 0.1675(2) -0.0762(2) 0.15921(16) 0.0419(8) Uani 1 1 d . . .
H11A H 0.1577 -0.1448 0.1631 0.050 Uiso 1 1 calc R . .
H11B H 0.1808 -0.0627 0.1109 0.050 Uiso 1 1 calc R . .
C13 C 0.06578(17) 0.1005(2) 0.10247(14) 0.0299(7) Uani 1 1 d . . .
H13 H 0.0270 0.0590 0.0812 0.036 Uiso 1 1 calc R . .
C14 C 0.08462(17) 0.1866(2) 0.06724(14) 0.0281(6) Uani 1 1 d . . .
C15 C 0.03774(19) 0.2079(2) 0.00929(15) 0.0381(8) Uani 1 1 d . . .
H15 H -0.0099 0.1708 -0.0023 0.046 Uiso 1 1 calc R . .
C16 C 0.0603(2) 0.2821(2) -0.03085(14) 0.0404(8) Uani 1 1 d . . .
C17 C 0.1316(2) 0.3349(2) -0.01767(14) 0.0386(8) Uani 1 1 d . . .
H17 H 0.1476 0.3845 -0.0474 0.046 Uiso 1 1 calc R . .
C18 C 0.1788(2) 0.3146(2) 0.03899(14) 0.0329(7) Uani 1 1 d . . .
H18 H 0.2280 0.3504 0.0481 0.039 Uiso 1 1 calc R . .
C19 C 0.15574(17) 0.24160(19) 0.08395(13) 0.0250(6) Uani 1 1 d . . .
C20 C 0.14614(18) 0.0606(2) 0.36314(17) 0.0344(7) Uani 1 1 d . . .
Fe1 Fe 0.17466(2) 0.15613(3) 0.220650(18) 0.02373(13) Uani 1 1 d . . .
N1 N 0.28147(13) 0.21005(16) 0.26827(10) 0.0241(5) Uani 1 1 d . . .
N2 N 0.26939(15) 0.04842(16) 0.19585(11) 0.0292(6) Uani 1 1 d . . .
H1N2 H 0.2833 0.0578 0.1503 0.035 Uiso 1 1 calc R . .
N3 N 0.09611(14) 0.07427(16) 0.15966(11) 0.0279(5) Uani 1 1 d . . .
N4 N 0.14501(16) 0.07983(17) 0.30773(13) 0.0365(6) Uani 1 1 d . . .
N5 N 0.15195(16) 0.42357(16) 0.51285(12) 0.0326(6) Uani 1 1 d . . .
N6 N 0.0099(2) 0.3041(3) -0.09008(16) 0.0631(10) Uani 1 1 d . . .
O1 O 0.11494(11) 0.26309(13) 0.25765(9) 0.0272(4) Uani 1 1 d . . .
O2 O 0.20093(12) 0.22592(13) 0.13769(9) 0.0264(4) Uani 1 1 d . . .
O3 O 0.22019(14) 0.41828(16) 0.54154(10) 0.0428(6) Uani 1 1 d . . .
O5 O -0.0552(3) 0.2582(2) -0.09865(19) 0.1171(15) Uani 1 1 d . . .
S1 S 0.14810(6) 0.03035(8) 0.44312(4) 0.0566(3) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C12 N3 1.474(4) . ?
C12 C11 1.513(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O4 N5 1.230(3) . ?
O6 N6 1.226(4) . ?
C1 O1 1.303(3) . ?
C1 C2 1.413(4) . ?
C1 C6 1.423(4) . ?
C2 C3 1.369(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(4) . ?
C4 N5 1.450(4) . ?
C5 C6 1.395(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.450(4) . ?
C7 N1 1.277(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.459(3) . ?
C8 C9 1.508(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.481(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.485(4) . ?
C10 C11 1.504(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 N3 1.278(4) . ?
C13 C14 1.438(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(4) . ?
C14 C19 1.414(4) . ?
C15 C16 1.365(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(5) . ?
C16 N6 1.447(4) . ?
C17 C18 1.373(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.411(4) . ?
C18 H18 0.9500 . ?
C19 O2 1.296(3) . ?
C20 N4 1.122(4) . ?
C20 S1 1.628(3) . ?
Fe1 O1 1.9345(18) . ?
Fe1 O2 1.9525(18) . ?
Fe1 N4 2.079(3) . ?
Fe1 N1 2.085(2) . ?
Fe1 N3 2.085(2) . ?
Fe1 N2 2.203(2) . ?
N2 H1N2 0.9300 . ?
N5 O3 1.225(3) . ?
N6 O5 1.235(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 C12 C11 108.4(2) . . ?
N3 C12 H12A 110.0 . . ?
C11 C12 H12A 110.0 . . ?
N3 C12 H12B 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
O1 C1 C2 119.3(2) . . ?
O1 C1 C6 122.7(2) . . ?
C2 C1 C6 118.0(2) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.4(2) . . ?
C5 C4 N5 118.4(3) . . ?
C3 C4 N5 120.2(2) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.6(2) . . ?
C5 C6 C7 117.5(2) . . ?
C1 C6 C7 122.8(2) . . ?
N1 C7 C6 124.4(2) . . ?
N1 C7 H7 117.8 . . ?
C6 C7 H7 117.8 . . ?
N1 C8 C9 107.1(2) . . ?
N1 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
N1 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.5 . . ?
N2 C9 C8 108.7(2) . . ?
N2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N2 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C11 114.0(2) . . ?
N2 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 116.2(3) . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.4 . . ?
N3 C13 C14 126.3(3) . . ?
N3 C13 H13 116.8 . . ?
C14 C13 H13 116.8 . . ?
C15 C14 C19 119.8(3) . . ?
C15 C14 C13 117.8(3) . . ?
C19 C14 C13 121.7(2) . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 121.8(3) . . ?
C15 C16 N6 119.0(3) . . ?
C17 C16 N6 119.2(3) . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.3(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
O2 C19 C18 119.5(2) . . ?
O2 C19 C14 122.5(2) . . ?
C18 C19 C14 118.0(2) . . ?
N4 C20 S1 178.8(3) . . ?
O1 Fe1 O2 91.08(8) . . ?
O1 Fe1 N4 89.43(9) . . ?
O2 Fe1 N4 178.73(9) . . ?
O1 Fe1 N1 86.70(8) . . ?
O2 Fe1 N1 90.75(8) . . ?
N4 Fe1 N1 90.45(9) . . ?
O1 Fe1 N3 111.12(8) . . ?
O2 Fe1 N3 86.14(8) . . ?
N4 Fe1 N3 92.59(9) . . ?
N1 Fe1 N3 161.94(9) . . ?
O1 Fe1 N2 164.87(8) . . ?
O2 Fe1 N2 91.29(8) . . ?
N4 Fe1 N2 88.52(9) . . ?
N1 Fe1 N2 78.32(9) . . ?
N3 Fe1 N2 83.96(9) . . ?
C7 N1 C8 121.7(2) . . ?
C7 N1 Fe1 124.32(18) . . ?
C8 N1 Fe1 113.09(17) . . ?
C9 N2 C10 111.1(2) . . ?
C9 N2 Fe1 109.76(17) . . ?
C10 N2 Fe1 117.17(19) . . ?
C9 N2 H1N2 106.0 . . ?
C10 N2 H1N2 106.0 . . ?
Fe1 N2 H1N2 106.0 . . ?
C13 N3 C12 116.6(2) . . ?
C13 N3 Fe1 124.62(19) . . ?
C12 N3 Fe1 117.87(19) . . ?
C20 N4 Fe1 157.1(3) . . ?
O3 N5 O4 122.7(2) . . ?
O3 N5 C4 119.0(2) . . ?
O4 N5 C4 118.3(3) . . ?
O6 N6 O5 123.4(3) . . ?
O6 N6 C16 119.1(4) . . ?
O5 N6 C16 117.5(4) . . ?
C1 O1 Fe1 127.05(16) . . ?
C19 O2 Fe1 130.40(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 995960'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(azido)-(N,N'-bis(3-ethoxy-2-oxido-benzylidene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H29 Fe N6 O4'
_chemical_formula_weight         509.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.0321(9)
_cell_length_b                   11.3322(9)
_cell_length_c                   18.9441(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.974(3)
_cell_angle_gamma                90
_cell_volume                     2350.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    32786
_cell_measurement_theta_min      4.133
_cell_measurement_theta_max      26.367

_exptl_crystal_description       plate
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.684
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray source'
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_probe          X-ray
_diffrn_detector                 'APEXII CCD camera'
_diffrn_measurement_device       'X8 APEX-II'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            36191
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.133
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4764
_reflns_number_gt                4380
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0312P)²+1.4163P] 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         4764
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0679
_refine_ls_wR_factor_gt          0.0656
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.87946(2) 0.76577(2) 0.06121(2) 0.01162(7) Uani 1 1 d . . . . .
O1 O 1.04654(9) 0.81730(8) 0.04964(5) 0.0144(2) Uani 1 1 d . . . . .
O2 O 0.93279(9) 0.66400(8) 0.14067(5) 0.0144(2) Uani 1 1 d . . . . .
O3 O 1.27601(9) 0.84254(9) 0.12139(5) 0.0197(2) Uani 1 1 d . . . . .
O4 O 0.95235(9) 0.47189(8) 0.22026(5) 0.0152(2) Uani 1 1 d . . . . .
N1 N 0.89058(11) 0.67220(10) -0.03371(6) 0.0137(2) Uani 1 1 d . . . . .
N2 N 0.79741(10) 0.90698(10) -0.00984(6) 0.0143(2) Uani 1 1 d . . . . .
H2 H 0.8643 0.9436 -0.0336 0.017 Uiso 1 1 calc R U . . .
N3 N 0.87306(10) 0.90512(10) 0.13325(6) 0.0137(2) Uani 1 1 d . . . . .
N4 N 0.70104(11) 0.71778(11) 0.06610(6) 0.0174(3) Uani 1 1 d . . . . .
N5 N 0.66789(10) 0.65388(10) 0.11043(6) 0.0151(2) Uani 1 1 d . . . . .
N6 N 0.63220(12) 0.59210(12) 0.15187(7) 0.0233(3) Uani 1 1 d . . . . .
C1 C 1.13149(13) 0.74182(12) 0.03641(7) 0.0140(3) Uani 1 1 d . . . . .
C2 C 1.25191(14) 0.75376(13) 0.07160(7) 0.0173(3) Uani 1 1 d . . . . .
C3 C 1.34613(14) 0.68513(14) 0.05314(8) 0.0221(3) Uani 1 1 d . . . . .
H3 H 1.4261 0.6954 0.0773 0.027 Uiso 1 1 calc R U . . .
C4 C 1.32566(14) 0.60058(14) -0.00073(8) 0.0232(3) Uani 1 1 d . . . . .
H4 H 1.3917 0.5558 -0.0145 0.028 Uiso 1 1 calc R U . . .
C5 C 1.20902(14) 0.58294(13) -0.03364(8) 0.0194(3) Uani 1 1 d . . . . .
H5 H 1.1945 0.5249 -0.0699 0.023 Uiso 1 1 calc R U . . .
C6 C 1.11075(13) 0.65002(12) -0.01417(7) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.99038(13) 0.62851(12) -0.05150(7) 0.0148(3) Uani 1 1 d . . . . .
H7 H 0.9845 0.5786 -0.0920 0.018 Uiso 1 1 calc R U . . .
C8 C 0.77897(13) 0.65859(13) -0.08377(7) 0.0171(3) Uani 1 1 d . . . . .
H8A H 0.7124 0.6274 -0.0585 0.020 Uiso 1 1 calc R U . . .
H8B H 0.7935 0.6018 -0.1215 0.020 Uiso 1 1 calc R U . . .
C9 C 0.74168(14) 0.77827(13) -0.11704(7) 0.0182(3) Uani 1 1 d . . . . .
H9A H 0.8121 0.8110 -0.1384 0.022 Uiso 1 1 calc R U . . .
H9B H 0.6748 0.7654 -0.1561 0.022 Uiso 1 1 calc R U . . .
C10 C 0.69971(13) 0.86979(13) -0.06646(7) 0.0168(3) Uani 1 1 d . . . . .
H10A H 0.6694 0.9401 -0.0942 0.020 Uiso 1 1 calc R U . . .
H10B H 0.6307 0.8369 -0.0439 0.020 Uiso 1 1 calc R U . . .
C11 C 0.75077(13) 0.99778(12) 0.03611(7) 0.0165(3) Uani 1 1 d . . . . .
H11A H 0.6738 0.9704 0.0526 0.020 Uiso 1 1 calc R U . . .
H11B H 0.7339 1.0719 0.0090 0.020 Uiso 1 1 calc R U . . .
C12 C 0.84616(13) 1.01946(12) 0.09926(7) 0.0164(3) Uani 1 1 d . . . . .
H12A H 0.9209 1.0536 0.0834 0.020 Uiso 1 1 calc R U . . .
H12B H 0.8146 1.0750 0.1330 0.020 Uiso 1 1 calc R U . . .
C13 C 0.88026(12) 0.89547(12) 0.20117(7) 0.0142(3) Uani 1 1 d . . . . .
H13 H 0.8714 0.9655 0.2276 0.017 Uiso 1 1 calc R U . . .
C14 C 0.90073(12) 0.78675(12) 0.24068(7) 0.0138(3) Uani 1 1 d . . . . .
C15 C 0.89403(13) 0.79426(13) 0.31483(7) 0.0158(3) Uani 1 1 d . . . . .
H15 H 0.8796 0.8684 0.3356 0.019 Uiso 1 1 calc R U . . .
C16 C 0.90812(13) 0.69591(13) 0.35658(7) 0.0170(3) Uani 1 1 d . . . . .
H16 H 0.9038 0.7017 0.4062 0.020 Uiso 1 1 calc R U . . .
C17 C 0.92901(12) 0.58637(13) 0.32599(7) 0.0153(3) Uani 1 1 d . . . . .
H17 H 0.9390 0.5181 0.3552 0.018 Uiso 1 1 calc R U . . .
C18 C 0.93530(12) 0.57617(12) 0.25381(7) 0.0133(3) Uani 1 1 d . . . . .
C19 C 0.92254(12) 0.67716(12) 0.20877(7) 0.0125(3) Uani 1 1 d . . . . .
C20 C 1.21787(14) 0.82515(14) 0.18525(7) 0.0212(3) Uani 1 1 d . . . . .
H20A H 1.2688 0.7732 0.2188 0.025 Uiso 1 1 calc R U . . .
H20B H 1.1371 0.7873 0.1732 0.025 Uiso 1 1 calc R U . . .
C21 C 1.20292(15) 0.94339(15) 0.21865(8) 0.0271(3) Uani 1 1 d . . . . .
H21A H 1.2832 0.9805 0.2300 0.041 Uiso 1 1 calc R U . . .
H21B H 1.1648 0.9334 0.2624 0.041 Uiso 1 1 calc R U . . .
H21C H 1.1511 0.9936 0.1854 0.041 Uiso 1 1 calc R U . . .
C22 C 0.94694(13) 0.36663(12) 0.26203(7) 0.0161(3) Uani 1 1 d . . . . .
H22A H 0.8701 0.3647 0.2841 0.019 Uiso 1 1 calc R U . . .
H22B H 1.0165 0.3642 0.3003 0.019 Uiso 1 1 calc R U . . .
C23 C 0.95246(16) 0.26330(13) 0.21294(8) 0.0233(3) Uani 1 1 d . . . . .
H23A H 0.8848 0.2681 0.1744 0.035 Uiso 1 1 calc R U . . .
H23B H 0.9459 0.1898 0.2395 0.035 Uiso 1 1 calc R U . . .
H23C H 1.0302 0.2645 0.1928 0.035 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
Fe1 O2 1.9307(9) . ?
Fe1 O1 1.9710(10) . ?
Fe1 N4 2.0549(12) . ?
Fe1 N3 2.0939(11) . ?
Fe1 N1 2.1039(11) . ?
Fe1 N2 2.2127(11) . ?
O1 C1 1.3153(17) . ?
O2 C19 1.3171(15) . ?
O3 C2 1.3827(18) . ?
O3 C20 1.4499(16) . ?
O4 C18 1.3655(16) . ?
O4 C22 1.4367(16) . ?
N1 C7 1.2888(18) . ?
N1 C8 1.4682(17) . ?
N2 C11 1.4798(17) . ?
N2 C10 1.4862(17) . ?
N2 H2 1.0000 . ?
N3 C13 1.2842(17) . ?
N3 C12 1.4613(17) . ?
N4 N5 1.1992(17) . ?
N5 N6 1.1560(17) . ?
C1 C6 1.4140(19) . ?
C1 C2 1.419(2) . ?
C2 C3 1.377(2) . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4094(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.447(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.531(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5218(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.514(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.4450(19) . ?
C13 H13 0.9500 . ?
C14 C19 1.4145(19) . ?
C14 C15 1.4182(18) . ?
C15 C16 1.365(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.401(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3823(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.4242(19) . ?
C20 C21 1.499(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.501(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 93.62(4) . . ?
O2 Fe1 N4 90.55(4) . . ?
O1 Fe1 N4 175.74(4) . . ?
O2 Fe1 N3 88.48(4) . . ?
O1 Fe1 N3 87.42(4) . . ?
N4 Fe1 N3 93.55(5) . . ?
O2 Fe1 N1 108.75(4) . . ?
O1 Fe1 N1 84.37(4) . . ?
N4 Fe1 N1 93.48(5) . . ?
N3 Fe1 N1 161.30(4) . . ?
O2 Fe1 N2 165.88(4) . . ?
O1 Fe1 N2 92.13(4) . . ?
N4 Fe1 N2 84.00(5) . . ?
N3 Fe1 N2 78.90(4) . . ?
N1 Fe1 N2 84.64(4) . . ?
C1 O1 Fe1 121.74(9) . . ?
C19 O2 Fe1 129.93(9) . . ?
C2 O3 C20 113.72(11) . . ?
C18 O4 C22 116.42(10) . . ?
C7 N1 C8 117.83(11) . . ?
C7 N1 Fe1 123.88(10) . . ?
C8 N1 Fe1 118.27(9) . . ?
C11 N2 C10 110.38(11) . . ?
C11 N2 Fe1 106.90(8) . . ?
C10 N2 Fe1 116.18(9) . . ?
C11 N2 H2 107.7 . . ?
C10 N2 H2 107.7 . . ?
Fe1 N2 H2 107.7 . . ?
C13 N3 C12 120.10(12) . . ?
C13 N3 Fe1 125.88(10) . . ?
C12 N3 Fe1 113.74(8) . . ?
N5 N4 Fe1 124.51(10) . . ?
N6 N5 N4 177.75(15) . . ?
O1 C1 C6 123.18(13) . . ?
O1 C1 C2 119.78(13) . . ?
C6 C1 C2 116.99(13) . . ?
C3 C2 O3 119.72(14) . . ?
C3 C2 C1 121.30(14) . . ?
O3 C2 C1 118.78(13) . . ?
C2 C3 C4 120.83(14) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 119.34(14) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.69(14) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.52(13) . . ?
C5 C6 C7 118.07(13) . . ?
C1 C6 C7 121.23(12) . . ?
N1 C7 C6 124.74(12) . . ?
N1 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
N1 C8 C9 109.59(11) . . ?
N1 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C8 115.57(11) . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
N2 C10 C9 113.47(11) . . ?
N2 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C12 108.64(11) . . ?
N2 C11 H11A 110.0 . . ?
C12 C11 H11A 110.0 . . ?
N2 C11 H11B 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.3 . . ?
N3 C12 C11 106.78(11) . . ?
N3 C12 H12A 110.4 . . ?
C11 C12 H12A 110.4 . . ?
N3 C12 H12B 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
N3 C13 C14 125.33(13) . . ?
N3 C13 H13 117.3 . . ?
C14 C13 H13 117.3 . . ?
C19 C14 C15 120.53(13) . . ?
C19 C14 C13 123.45(12) . . ?
C15 C14 C13 115.99(12) . . ?
C16 C15 C14 120.61(13) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.78(12) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.93(13) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
O4 C18 C17 123.99(12) . . ?
O4 C18 C19 115.20(11) . . ?
C17 C18 C19 120.81(12) . . ?
O2 C19 C14 123.87(12) . . ?
O2 C19 C18 118.80(12) . . ?
C14 C19 C18 117.33(12) . . ?
O3 C20 C21 108.25(12) . . ?
O3 C20 H20A 110.0 . . ?
C21 C20 H20A 110.0 . . ?
O3 C20 H20B 110.0 . . ?
C21 C20 H20B 110.0 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 C23 107.40(11) . . ?
O4 C22 H22A 110.2 . . ?
C23 C22 H22A 110.2 . . ?
O4 C22 H22B 110.2 . . ?
C23 C22 H22B 110.2 . . ?
H22A C22 H22B 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1 C1 C6 44.56(16) . . . . ?
Fe1 O1 C1 C2 -138.14(11) . . . . ?
C20 O3 C2 C3 -116.91(14) . . . . ?
C20 O3 C2 C1 68.16(16) . . . . ?
O1 C1 C2 C3 -172.38(13) . . . . ?
C6 C1 C2 C3 5.1(2) . . . . ?
O1 C1 C2 O3 2.47(19) . . . . ?
C6 C1 C2 O3 179.92(11) . . . . ?
O3 C2 C3 C4 -175.31(13) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -2.5(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 4.0(2) . . . . ?
C4 C5 C6 C7 179.12(13) . . . . ?
O1 C1 C6 C5 170.59(12) . . . . ?
C2 C1 C6 C5 -6.77(19) . . . . ?
O1 C1 C6 C7 -4.4(2) . . . . ?
C2 C1 C6 C7 178.29(12) . . . . ?
C8 N1 C7 C6 169.68(12) . . . . ?
Fe1 N1 C7 C6 -8.48(19) . . . . ?
C5 C6 C7 N1 171.01(13) . . . . ?
C1 C6 C7 N1 -13.9(2) . . . . ?
C7 N1 C8 C9 -109.02(14) . . . . ?
Fe1 N1 C8 C9 69.24(12) . . . . ?
N1 C8 C9 C10 -67.33(16) . . . . ?
C11 N2 C10 C9 178.70(11) . . . . ?
Fe1 N2 C10 C9 -59.42(13) . . . . ?
C8 C9 C10 N2 64.76(16) . . . . ?
C10 N2 C11 C12 171.42(11) . . . . ?
Fe1 N2 C11 C12 44.21(12) . . . . ?
C13 N3 C12 C11 -134.98(13) . . . . ?
Fe1 N3 C12 C11 39.29(13) . . . . ?
N2 C11 C12 N3 -55.33(14) . . . . ?
C12 N3 C13 C14 177.04(12) . . . . ?
Fe1 N3 C13 C14 3.5(2) . . . . ?
N3 C13 C14 C19 3.8(2) . . . . ?
N3 C13 C14 C15 -174.26(13) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C13 C14 C15 C16 177.91(13) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C18 -0.2(2) . . . . ?
C22 O4 C18 C17 8.47(18) . . . . ?
C22 O4 C18 C19 -170.84(11) . . . . ?
C16 C17 C18 O4 -178.31(13) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
Fe1 O2 C19 C14 -19.44(19) . . . . ?
Fe1 O2 C19 C18 161.30(9) . . . . ?
C15 C14 C19 O2 -178.32(12) . . . . ?
C13 C14 C19 O2 3.7(2) . . . . ?
C15 C14 C19 C18 0.95(19) . . . . ?
C13 C14 C19 C18 -177.02(12) . . . . ?
O4 C18 C19 O2 -2.68(18) . . . . ?
C17 C18 C19 O2 177.99(12) . . . . ?
O4 C18 C19 C14 178.01(12) . . . . ?
C17 C18 C19 C14 -1.33(19) . . . . ?
C2 O3 C20 C21 -155.36(12) . . . . ?
C18 O4 C22 C23 173.18(12) . . . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 995961'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis(3,5-di(terc-buthyl)-2-oxido-benzylidene)-1,6-diamino-4-azahexane)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H53 Fe N4 O2 S'
_chemical_formula_weight         661.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   18.2879(7)
_cell_length_b                   11.8974(4)
_cell_length_c                   17.3763(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.903(4)
_cell_angle_gamma                90.00
_cell_volume                     3753.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8852
_cell_measurement_theta_min      2.9496
_cell_measurement_theta_max      33.1508

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1420
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8706
_exptl_absorpt_correction_T_max  0.9038
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
face-indexed (CrysAlis RED; Oxford Diffraction, 2006)
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.3611
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24769
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0733
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6588
_reflns_number_gt                4301
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  ' enCIFer (Allen et al., 2004)'

_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)+(0.0503P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6588
_refine_ls_number_parameters     404
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.500 100 13 ' '
2 0.500 0.500 1.000 100 13 ' '
_platon_squeeze_details          
;
Total Potential Solvent Accessible Void Vol ...   202.8 Ang^3
Electron Count / Cell =     25 
;


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
C28 C 0.5228(4) 0.3039(7) 0.2968(6) 0.0618(10) Uani 0.482(3) 1 d PD A 1
H28A H 0.5171 0.3567 0.2531 0.093 Uiso 0.482(3) 1 calc PR A 1
H28B H 0.5697 0.2638 0.2974 0.093 Uiso 0.482(3) 1 calc PR A 1
H28C H 0.5223 0.3454 0.3454 0.093 Uiso 0.482(3) 1 calc PR A 1
C27 C 0.4851(4) 0.1404(7) 0.2161(4) 0.0618(10) Uani 0.482(3) 1 d PD A 1
H27A H 0.4488 0.0802 0.2046 0.093 Uiso 0.482(3) 1 calc PR A 1
H27B H 0.5336 0.1074 0.2321 0.093 Uiso 0.482(3) 1 calc PR A 1
H27C H 0.4872 0.1865 0.1697 0.093 Uiso 0.482(3) 1 calc PR A 1
C26 C 0.4550(4) 0.1390(8) 0.3481(5) 0.0618(10) Uani 0.482(3) 1 d PD A 1
H26A H 0.4097 0.0951 0.3359 0.093 Uiso 0.482(3) 1 calc PR A 1
H26B H 0.4539 0.1775 0.3978 0.093 Uiso 0.482(3) 1 calc PR A 1
H26C H 0.4977 0.0886 0.3516 0.093 Uiso 0.482(3) 1 calc PR A 1
C28B C 0.5243(4) 0.2540(7) 0.2520(5) 0.0618(10) Uani 0.518(3) 1 d PD A 2
H28D H 0.5253 0.3360 0.2472 0.093 Uiso 0.518(3) 1 calc PR A 2
H28E H 0.5219 0.2199 0.2004 0.093 Uiso 0.518(3) 1 calc PR A 2
H28F H 0.5691 0.2286 0.2840 0.093 Uiso 0.518(3) 1 calc PR A 2
C1 C 0.25733(14) 0.3932(2) 0.19611(15) 0.0195(6) Uani 1 1 d . . .
C2 C 0.31857(14) 0.3911(2) 0.15296(15) 0.0219(6) Uani 1 1 d . . .
C3 C 0.38125(15) 0.3353(2) 0.18487(17) 0.0290(7) Uani 1 1 d . . .
H3 H 0.4224 0.3349 0.1563 0.035 Uiso 1 1 calc R . .
C4 C 0.38850(15) 0.2792(2) 0.25652(18) 0.0325(7) Uani 1 1 d . A .
C5 C 0.32868(15) 0.2808(2) 0.29658(17) 0.0281(7) Uani 1 1 d . . .
H5 H 0.3315 0.2431 0.3450 0.034 Uiso 1 1 calc R . .
C6 C 0.26329(15) 0.3363(2) 0.26838(15) 0.0222(6) Uani 1 1 d . . .
C7 C 0.20516(15) 0.3366(2) 0.31785(16) 0.0243(6) Uani 1 1 d . . .
H7 H 0.2144 0.2961 0.3651 0.029 Uiso 1 1 calc R . .
C8 C 0.09207(15) 0.3864(2) 0.36384(16) 0.0272(7) Uani 1 1 d . . .
H8A H 0.0999 0.4550 0.3961 0.033 Uiso 1 1 calc R . .
H8B H 0.1010 0.3201 0.3980 0.033 Uiso 1 1 calc R . .
C9 C 0.01459(15) 0.3840(2) 0.32377(17) 0.0281(7) Uani 1 1 d . . .
H9A H 0.0042 0.3100 0.2988 0.034 Uiso 1 1 calc R . .
H9B H -0.0207 0.3958 0.3620 0.034 Uiso 1 1 calc R . .
C10 C -0.06705(14) 0.4651(2) 0.21780(16) 0.0281(7) Uani 1 1 d . . .
H10A H -0.1059 0.4706 0.2527 0.034 Uiso 1 1 calc R . .
H10B H -0.0714 0.3902 0.1927 0.034 Uiso 1 1 calc R . .
C11 C -0.08036(15) 0.5548(2) 0.15573(16) 0.0279(7) Uani 1 1 d . . .
H11A H -0.0733 0.6293 0.1809 0.033 Uiso 1 1 calc R . .
H11B H -0.1324 0.5501 0.1324 0.033 Uiso 1 1 calc R . .
C12 C -0.03117(14) 0.5484(2) 0.09043(16) 0.0247(7) Uani 1 1 d . . .
H12A H -0.0323 0.4715 0.0687 0.030 Uiso 1 1 calc R . .
H12B H -0.0493 0.6012 0.0483 0.030 Uiso 1 1 calc R . .
C13 C 0.07114(14) 0.6721(2) 0.10125(15) 0.0197(6) Uani 1 1 d . . .
H13 H 0.0459 0.7081 0.0570 0.024 Uiso 1 1 calc R . .
C14 C 0.13570(13) 0.7276(2) 0.13916(14) 0.0166(6) Uani 1 1 d . . .
C15 C 0.16224(14) 0.8215(2) 0.10167(15) 0.0199(6) Uani 1 1 d . . .
H15 H 0.1406 0.8403 0.0509 0.024 Uiso 1 1 calc R . .
C16 C 0.21861(14) 0.8863(2) 0.13679(15) 0.0198(6) Uani 1 1 d . . .
C17 C 0.24791(14) 0.8550(2) 0.21198(15) 0.0210(6) Uani 1 1 d . . .
H17 H 0.2880 0.8979 0.2363 0.025 Uiso 1 1 calc R . .
C18 C 0.22318(14) 0.7665(2) 0.25359(15) 0.0195(6) Uani 1 1 d . . .
C19 C 0.16457(13) 0.7002(2) 0.21594(15) 0.0172(6) Uani 1 1 d . . .
C20 C 0.04064(15) 0.2504(2) 0.11393(15) 0.0226(6) Uani 1 1 d . . .
C21 C 0.31475(15) 0.4511(2) 0.07406(16) 0.0277(7) Uani 1 1 d . . .
C22 C 0.25067(17) 0.4045(3) 0.01822(17) 0.0434(9) Uani 1 1 d . . .
H22A H 0.2494 0.4421 -0.0321 0.065 Uiso 1 1 calc R . .
H22B H 0.2042 0.4180 0.0395 0.065 Uiso 1 1 calc R . .
H22C H 0.2574 0.3235 0.0116 0.065 Uiso 1 1 calc R . .
C23 C 0.30548(17) 0.5773(2) 0.08582(18) 0.0361(8) Uani 1 1 d . . .
H23A H 0.3468 0.6056 0.1217 0.054 Uiso 1 1 calc R . .
H23B H 0.2592 0.5914 0.1074 0.054 Uiso 1 1 calc R . .
H23C H 0.3045 0.6160 0.0359 0.054 Uiso 1 1 calc R . .
C24 C 0.38505(17) 0.4341(3) 0.03580(18) 0.0423(8) Uani 1 1 d . . .
H24A H 0.4269 0.4674 0.0684 0.064 Uiso 1 1 calc R . .
H24B H 0.3795 0.4705 -0.0152 0.064 Uiso 1 1 calc R . .
H24C H 0.3938 0.3535 0.0296 0.064 Uiso 1 1 calc R . .
C25 C 0.46052(17) 0.2209(3) 0.2880(2) 0.0514(10) Uani 1 1 d D . .
C26B C 0.4455(4) 0.1004(6) 0.3031(5) 0.0618(10) Uani 0.518(3) 1 d PD A 2
H26D H 0.4019 0.0944 0.3305 0.093 Uiso 0.518(3) 1 calc PR A 2
H26E H 0.4880 0.0675 0.3349 0.093 Uiso 0.518(3) 1 calc PR A 2
H26F H 0.4367 0.0599 0.2537 0.093 Uiso 0.518(3) 1 calc PR A 2
C27B C 0.4820(4) 0.2715(6) 0.3777(4) 0.0618(10) Uani 0.518(3) 1 d PD A 2
H27D H 0.4419 0.2552 0.4087 0.093 Uiso 0.518(3) 1 calc PR A 2
H27E H 0.4892 0.3530 0.3752 0.093 Uiso 0.518(3) 1 calc PR A 2
H27F H 0.5275 0.2360 0.4017 0.093 Uiso 0.518(3) 1 calc PR A 2
C29 C 0.25760(14) 0.7408(2) 0.33649(15) 0.0213(6) Uani 1 1 d . . .
C30 C 0.19966(15) 0.7550(2) 0.39273(15) 0.0268(7) Uani 1 1 d . . .
H30A H 0.1819 0.8328 0.3908 0.040 Uiso 1 1 calc R . .
H30B H 0.2218 0.7372 0.4455 0.040 Uiso 1 1 calc R . .
H30C H 0.1583 0.7041 0.3778 0.040 Uiso 1 1 calc R . .
C31 C 0.28754(15) 0.6204(2) 0.34038(16) 0.0282(7) Uani 1 1 d . . .
H31A H 0.3123 0.6055 0.3926 0.042 Uiso 1 1 calc R . .
H31B H 0.3227 0.6113 0.3025 0.042 Uiso 1 1 calc R . .
H31C H 0.2467 0.5674 0.3286 0.042 Uiso 1 1 calc R . .
C32 C 0.32176(16) 0.8195(2) 0.36366(16) 0.0300(7) Uani 1 1 d . . .
H32A H 0.3040 0.8972 0.3631 0.045 Uiso 1 1 calc R . .
H32B H 0.3598 0.8126 0.3288 0.045 Uiso 1 1 calc R . .
H32C H 0.3425 0.7991 0.4164 0.045 Uiso 1 1 calc R . .
C33 C 0.24905(15) 0.9906(2) 0.10007(16) 0.0280(7) Uani 1 1 d . . .
C34 C 0.20599(16) 1.0185(2) 0.02163(16) 0.0313(7) Uani 1 1 d . . .
H34A H 0.1542 1.0317 0.0282 0.047 Uiso 1 1 calc R . .
H34B H 0.2094 0.9554 -0.0140 0.047 Uiso 1 1 calc R . .
H34C H 0.2267 1.0861 0.0004 0.047 Uiso 1 1 calc R . .
C35 C 0.2431(2) 1.0916(2) 0.15309(18) 0.0459(9) Uani 1 1 d . . .
H35A H 0.2651 1.1576 0.1311 0.069 Uiso 1 1 calc R . .
H35B H 0.2692 1.0755 0.2045 0.069 Uiso 1 1 calc R . .
H35C H 0.1911 1.1066 0.1577 0.069 Uiso 1 1 calc R . .
C36 C 0.32920(17) 0.9686(3) 0.0888(2) 0.0518(10) Uani 1 1 d . . .
H36A H 0.3318 0.9050 0.0534 0.078 Uiso 1 1 calc R . .
H36B H 0.3574 0.9510 0.1390 0.078 Uiso 1 1 calc R . .
H36C H 0.3500 1.0356 0.0668 0.078 Uiso 1 1 calc R . .
Fe1 Fe 0.10477(2) 0.47567(3) 0.20432(2) 0.01980(12) Uani 1 1 d . . .
N1 N 0.14266(12) 0.38552(18) 0.30482(12) 0.0220(5) Uani 1 1 d . . .
N2 N 0.00590(11) 0.47355(18) 0.26477(12) 0.0221(5) Uani 1 1 d . . .
H1N2 H 0.0059 0.5411 0.2917 0.026 Uiso 1 1 calc R . .
N3 N 0.04450(11) 0.57813(18) 0.12197(12) 0.0209(5) Uani 1 1 d . . .
N4 N 0.06021(13) 0.3328(2) 0.14557(14) 0.0300(6) Uani 1 1 d . . .
O1 O 0.19746(9) 0.44805(15) 0.16943(10) 0.0237(4) Uani 1 1 d . . .
O2 O 0.13599(9) 0.61741(14) 0.25319(10) 0.0218(4) Uani 1 1 d . . .
S1 S 0.01204(4) 0.13598(6) 0.06858(4) 0.0322(2) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C28 C25 1.502(8) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C27 C25 1.677(8) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C26 C25 1.442(8) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C28B C25 1.443(7) . ?
C28B H28D 0.9800 . ?
C28B H28E 0.9800 . ?
C28B H28F 0.9800 . ?
C1 O1 1.310(3) . ?
C1 C6 1.420(4) . ?
C1 C2 1.421(4) . ?
C2 C3 1.381(4) . ?
C2 C21 1.540(4) . ?
C3 C4 1.405(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.366(4) . ?
C4 C25 1.530(4) . ?
C5 C6 1.402(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.445(4) . ?
C7 N1 1.278(3) . ?
C7 H7 0.9500 . ?
C8 N1 1.461(3) . ?
C8 C9 1.502(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N2 1.474(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.481(3) . ?
C10 C11 1.517(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.532(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N3 1.469(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N3 1.288(3) . ?
C13 C14 1.441(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.408(3) . ?
C14 C19 1.413(4) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.402(4) . ?
C16 C33 1.531(4) . ?
C17 C18 1.383(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.426(4) . ?
C18 C29 1.532(4) . ?
C19 O2 1.320(3) . ?
C20 N4 1.159(3) . ?
C20 S1 1.628(3) . ?
C21 C23 1.527(4) . ?
C21 C24 1.530(4) . ?
C21 C22 1.533(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26B 1.489(8) . ?
C25 C27B 1.674(7) . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 0.9800 . ?
C29 C32 1.531(4) . ?
C29 C31 1.532(4) . ?
C29 C30 1.535(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C36 1.525(4) . ?
C33 C35 1.526(4) . ?
C33 C34 1.526(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Fe1 O1 1.8964(18) . ?
Fe1 O2 1.9428(17) . ?
Fe1 N3 2.090(2) . ?
Fe1 N1 2.095(2) . ?
Fe1 N4 2.096(2) . ?
Fe1 N2 2.198(2) . ?
N2 H1N2 0.9300 . ?

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
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C28B H28D 109.5 . . ?
C25 C28B H28E 109.5 . . ?
H28D C28B H28E 109.5 . . ?
C25 C28B H28F 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
O1 C1 C6 121.5(2) . . ?
O1 C1 C2 120.0(2) . . ?
C6 C1 C2 118.5(2) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 C21 121.8(2) . . ?
C1 C2 C21 120.5(2) . . ?
C2 C3 C4 124.7(3) . . ?
C2 C3 H3 117.6 . . ?
C4 C3 H3 117.6 . . ?
C5 C4 C3 116.7(3) . . ?
C5 C4 C25 122.1(3) . . ?
C3 C4 C25 121.2(3) . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 C7 116.8(2) . . ?
C1 C6 C7 122.8(2) . . ?
N1 C7 C6 127.0(3) . . ?
N1 C7 H7 116.5 . . ?
C6 C7 H7 116.5 . . ?
N1 C8 C9 108.4(2) . . ?
N1 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
C9 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N2 C9 C8 109.0(2) . . ?
N2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N2 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C11 113.6(2) . . ?
N2 C10 H10A 108.8 . . ?
C11 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C11 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 115.7(2) . . ?
C10 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
N3 C12 C11 108.8(2) . . ?
N3 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
N3 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N3 C13 C14 125.9(2) . . ?
N3 C13 H13 117.0 . . ?
C14 C13 H13 117.0 . . ?
C15 C14 C19 120.6(2) . . ?
C15 C14 C13 117.4(2) . . ?
C19 C14 C13 121.2(2) . . ?
C16 C15 C14 121.5(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 116.6(2) . . ?
C15 C16 C33 124.2(2) . . ?
C17 C16 C33 119.1(2) . . ?
C18 C17 C16 125.3(2) . . ?
C18 C17 H17 117.4 . . ?
C16 C17 H17 117.4 . . ?
C17 C18 C19 117.2(2) . . ?
C17 C18 C29 121.4(2) . . ?
C19 C18 C29 121.5(2) . . ?
O2 C19 C14 120.7(2) . . ?
O2 C19 C18 120.5(2) . . ?
C14 C19 C18 118.7(2) . . ?
N4 C20 S1 179.0(3) . . ?
C23 C21 C24 107.5(2) . . ?
C23 C21 C22 110.6(3) . . ?
C24 C21 C22 107.2(2) . . ?
C23 C21 C2 109.3(2) . . ?
C24 C21 C2 112.0(2) . . ?
C22 C21 C2 110.2(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C28B 129.0(5) . . ?
C26 C25 C26B 36.0(4) . . ?
C28B C25 C26B 121.0(5) . . ?
C26 C25 C28 119.3(5) . . ?
C28B C25 C28 38.9(4) . . ?
C26B C25 C28 140.3(4) . . ?
C26 C25 C4 115.7(4) . . ?
C28B C25 C4 115.3(4) . . ?
C26B C25 C4 109.3(4) . . ?
C28 C25 C4 110.3(4) . . ?
C26 C25 C27B 66.2(5) . . ?
C28B C25 C27B 101.2(5) . . ?
C26B C25 C27B 102.1(5) . . ?
C28 C25 C27B 65.1(5) . . ?
C4 C25 C27B 105.4(3) . . ?
C26 C25 C27 101.7(5) . . ?
C28B C25 C27 62.0(5) . . ?
C26B C25 C27 69.7(5) . . ?
C28 C25 C27 100.6(5) . . ?
C4 C25 C27 106.8(3) . . ?
C27B C25 C27 147.7(4) . . ?
C25 C26B H26D 109.5 . . ?
C25 C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C25 C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C25 C27B H27D 109.5 . . ?
C25 C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C25 C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
C32 C29 C18 112.4(2) . . ?
C32 C29 C31 107.6(2) . . ?
C18 C29 C31 109.4(2) . . ?
C32 C29 C30 107.4(2) . . ?
C18 C29 C30 109.9(2) . . ?
C31 C29 C30 110.2(2) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C36 C33 C35 110.6(3) . . ?
C36 C33 C34 108.9(2) . . ?
C35 C33 C34 107.6(2) . . ?
C36 C33 C16 108.5(2) . . ?
C35 C33 C16 109.3(2) . . ?
C34 C33 C16 111.9(2) . . ?
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 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O1 Fe1 O2 93.62(8) . . ?
O1 Fe1 N3 107.47(8) . . ?
O2 Fe1 N3 84.04(8) . . ?
O1 Fe1 N1 87.65(8) . . ?
O2 Fe1 N1 91.70(8) . . ?
N3 Fe1 N1 164.48(9) . . ?
O1 Fe1 N4 90.80(8) . . ?
O2 Fe1 N4 173.31(9) . . ?
N3 Fe1 N4 89.85(9) . . ?
N1 Fe1 N4 93.50(9) . . ?
O1 Fe1 N2 165.75(8) . . ?
O2 Fe1 N2 90.94(8) . . ?
N3 Fe1 N2 86.42(8) . . ?
N1 Fe1 N2 78.72(8) . . ?
N4 Fe1 N2 85.96(9) . . ?
C7 N1 C8 120.5(2) . . ?
C7 N1 Fe1 125.43(19) . . ?
C8 N1 Fe1 114.04(17) . . ?
C9 N2 C10 110.4(2) . . ?
C9 N2 Fe1 108.34(16) . . ?
C10 N2 Fe1 118.39(16) . . ?
C9 N2 H1N2 106.3 . . ?
C10 N2 H1N2 106.3 . . ?
Fe1 N2 H1N2 106.3 . . ?
C13 N3 C12 118.4(2) . . ?
C13 N3 Fe1 120.77(18) . . ?
C12 N3 Fe1 120.71(17) . . ?
C20 N4 Fe1 175.0(2) . . ?
C1 O1 Fe1 135.57(16) . . ?
C19 O2 Fe1 123.08(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 995962'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_6

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(isothiocyanato)-(N,N'-bis(3-ethoxy-2-oxido-benzylidene)-1,5-diamino-4-azapentene)-iron(iii)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H27 Fe N4 O4 S'
_chemical_formula_weight         511.39

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.5785(6)
_cell_length_b                   11.6541(5)
_cell_length_c                   18.2132(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.508(2)
_cell_angle_gamma                90
_cell_volume                     2356.33(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4558
_cell_measurement_theta_min      4.137
_cell_measurement_theta_max      26.372

_exptl_crystal_description       block
_exptl_crystal_colour            dark-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.766
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.915
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   'SADABS (Bruker, 2012)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode X-ray source'
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_probe          X-ray
_diffrn_detector                 'APEXII CCD camera'
_diffrn_measurement_device       'X8 APEX-II ULTRA'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         4.137
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4808
_reflns_number_gt                4040
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0363P)²+2.0533P] 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         4808
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0779
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.20341(2) 0.52971(2) 0.09397(2) 0.01120(9) Uani 1 1 d . . . . .
S1 S -0.07771(6) 0.39154(6) 0.22276(4) 0.03855(17) Uani 1 1 d . . . . .
O1 O 0.17377(11) 0.41042(11) 0.01587(7) 0.0133(3) Uani 1 1 d . . . . .
O2 O 0.35182(12) 0.45390(11) 0.14432(7) 0.0156(3) Uani 1 1 d . . . . .
O3 O 0.21349(13) 0.17919(12) -0.00334(8) 0.0199(3) Uani 1 1 d . . . . .
O4 O 0.51978(12) 0.29608(12) 0.17756(8) 0.0221(3) Uani 1 1 d . . . . .
N1 N 0.26239(14) 0.62470(14) 0.01224(9) 0.0145(3) Uani 1 1 d . . . . .
N2 N 0.06630(14) 0.66918(14) 0.05849(9) 0.0147(3) Uani 1 1 d . . . . .
H2 H -0.0132 0.6325 0.0334 0.018 Uiso 1 1 calc R U . . .
N3 N 0.26171(14) 0.65767(14) 0.18274(9) 0.0147(3) Uani 1 1 d . . . . .
N4 N 0.08507(14) 0.45316(14) 0.14672(10) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.25730(16) 0.37982(17) -0.01776(10) 0.0135(4) Uani 1 1 d . . . . .
C2 C 0.27769(17) 0.26271(17) -0.02861(11) 0.0160(4) Uani 1 1 d . . . . .
C3 C 0.36015(18) 0.22846(19) -0.06623(11) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.3736 0.1489 -0.0718 0.024 Uiso 1 1 calc R U . . .
C4 C 0.42386(19) 0.3087(2) -0.09609(12) 0.0234(5) Uani 1 1 d . . . . .
H4 H 0.4781 0.2845 -0.1236 0.028 Uiso 1 1 calc R U . . .
C5 C 0.40688(18) 0.4235(2) -0.08514(12) 0.0214(4) Uani 1 1 d . . . . .
H5 H 0.4503 0.4788 -0.1050 0.026 Uiso 1 1 calc R U . . .
C6 C 0.32657(17) 0.46016(17) -0.04509(11) 0.0158(4) Uani 1 1 d . . . . .
C7 C 0.30981(17) 0.58189(18) -0.03691(11) 0.0170(4) Uani 1 1 d . . . . .
H7 H 0.3355 0.6328 -0.0699 0.020 Uiso 1 1 calc R U . . .
C8 C 0.22956(18) 0.74600(17) 0.00872(12) 0.0187(4) Uani 1 1 d . . . . .
H8A H 0.2454 0.7832 -0.0363 0.022 Uiso 1 1 calc R U . . .
H8B H 0.2760 0.7865 0.0556 0.022 Uiso 1 1 calc R U . . .
C9 C 0.09517(18) 0.74780(17) 0.00209(11) 0.0173(4) Uani 1 1 d . . . . .
H9A H 0.0707 0.8268 0.0109 0.021 Uiso 1 1 calc R U . . .
H9B H 0.0490 0.7245 -0.0503 0.021 Uiso 1 1 calc R U . . .
C10 C 0.05703(18) 0.72769(18) 0.12877(11) 0.0185(4) Uani 1 1 d . . . . .
H10A H 0.0156 0.6770 0.1569 0.022 Uiso 1 1 calc R U . . .
H10B H 0.0089 0.7987 0.1148 0.022 Uiso 1 1 calc R U . . .
C11 C 0.18191(18) 0.75708(18) 0.17960(12) 0.0198(4) Uani 1 1 d . . . . .
H11A H 0.2139 0.8245 0.1587 0.024 Uiso 1 1 calc R U . . .
H11B H 0.1779 0.7763 0.2318 0.024 Uiso 1 1 calc R U . . .
C12 C 0.35684(17) 0.65278(17) 0.24044(11) 0.0165(4) Uani 1 1 d . . . . .
H12 H 0.3691 0.7143 0.2761 0.020 Uiso 1 1 calc R U . . .
C13 C 0.44600(17) 0.56355(17) 0.25612(11) 0.0157(4) Uani 1 1 d . . . . .
C14 C 0.54221(19) 0.57226(19) 0.32421(12) 0.0217(5) Uani 1 1 d . . . . .
H14 H 0.5463 0.6363 0.3571 0.026 Uiso 1 1 calc R U . . .
C15 C 0.62914(18) 0.4895(2) 0.34306(12) 0.0227(5) Uani 1 1 d . . . . .
H15 H 0.6922 0.4954 0.3895 0.027 Uiso 1 1 calc R U . . .
C16 C 0.62572(18) 0.39630(19) 0.29453(12) 0.0203(4) Uani 1 1 d . . . . .
H16 H 0.6879 0.3403 0.3073 0.024 Uiso 1 1 calc R U . . .
C17 C 0.53251(17) 0.38480(17) 0.22804(11) 0.0168(4) Uani 1 1 d . . . . .
C18 C 0.43939(17) 0.46877(17) 0.20752(11) 0.0144(4) Uani 1 1 d . . . . .
C19 C 0.61001(19) 0.20725(19) 0.19477(13) 0.0248(5) Uani 1 1 d . . . . .
H19A H 0.6153 0.1721 0.2451 0.030 Uiso 1 1 calc R U . . .
H19B H 0.6898 0.2393 0.1963 0.030 Uiso 1 1 calc R U . . .
C21 C 0.23320(19) 0.17598(17) 0.07878(12) 0.0192(4) Uani 1 1 d . . . . .
H21A H 0.1703 0.2209 0.0931 0.023 Uiso 1 1 calc R U . . .
H21B H 0.3128 0.2092 0.1053 0.023 Uiso 1 1 calc R U . . .
C22 C 0.2280(2) 0.05174(19) 0.10130(15) 0.0299(5) Uani 1 1 d . . . . .
H22A H 0.1479 0.0206 0.0761 0.045 Uiso 1 1 calc R U . . .
H22B H 0.2439 0.0462 0.1570 0.045 Uiso 1 1 calc R U . . .
H22C H 0.2889 0.0078 0.0854 0.045 Uiso 1 1 calc R U . . .
C20 C 0.5720(2) 0.1194(2) 0.13217(15) 0.0335(6) Uani 1 1 d . . . . .
H20A H 0.4938 0.0871 0.1321 0.050 Uiso 1 1 calc R U . . .
H20B H 0.6322 0.0579 0.1409 0.050 Uiso 1 1 calc R U . . .
H20C H 0.5652 0.1557 0.0826 0.050 Uiso 1 1 calc R U . . .
C23 C 0.0184(2) 0.42993(18) 0.17703(12) 0.0232(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 O2 1.9180(13) . ?
Fe1 O1 1.9485(13) . ?
Fe1 N4 2.0843(17) . ?
Fe1 N1 2.1178(16) . ?
Fe1 N3 2.1618(16) . ?
Fe1 N2 2.2353(16) . ?
S1 C23 1.630(2) . ?
O1 C1 1.332(2) . ?
O2 C18 1.311(2) . ?
O3 C2 1.381(2) . ?
O3 C21 1.448(2) . ?
O4 C17 1.363(2) . ?
O4 C19 1.441(2) . ?
N1 C7 1.277(3) . ?
N1 C8 1.461(3) . ?
N2 C10 1.481(2) . ?
N2 C9 1.484(2) . ?
N2 H2 1.0000 . ?
N3 C12 1.290(3) . ?
N3 C11 1.473(3) . ?
N4 C23 1.103(3) . ?
C1 C2 1.408(3) . ?
C1 C6 1.412(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.445(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.518(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.436(3) . ?
C12 H12 0.9500 . ?
C13 C18 1.404(3) . ?
C13 C14 1.416(3) . ?
C14 C15 1.366(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.425(3) . ?
C19 C20 1.503(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 C22 1.511(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 88.19(6) . . ?
O2 Fe1 N4 101.51(6) . . ?
O1 Fe1 N4 91.64(6) . . ?
O2 Fe1 N1 98.79(6) . . ?
O1 Fe1 N1 83.39(6) . . ?
N4 Fe1 N1 158.93(6) . . ?
O2 Fe1 N3 85.02(6) . . ?
O1 Fe1 N3 172.30(6) . . ?
N4 Fe1 N3 93.27(6) . . ?
N1 Fe1 N3 94.05(6) . . ?
O2 Fe1 N2 159.94(6) . . ?
O1 Fe1 N2 110.15(6) . . ?
N4 Fe1 N2 86.48(6) . . ?
N1 Fe1 N2 76.18(6) . . ?
N3 Fe1 N2 76.10(6) . . ?
C1 O1 Fe1 121.77(11) . . ?
C18 O2 Fe1 136.31(13) . . ?
C2 O3 C21 114.88(15) . . ?
C17 O4 C19 117.74(16) . . ?
C7 N1 C8 120.37(17) . . ?
C7 N1 Fe1 125.26(14) . . ?
C8 N1 Fe1 113.89(12) . . ?
C10 N2 C9 113.58(15) . . ?
C10 N2 Fe1 107.75(11) . . ?
C9 N2 Fe1 111.59(11) . . ?
C10 N2 H2 107.9 . . ?
C9 N2 H2 107.9 . . ?
Fe1 N2 H2 107.9 . . ?
C12 N3 C11 116.58(16) . . ?
C12 N3 Fe1 126.29(14) . . ?
C11 N3 Fe1 117.03(12) . . ?
C23 N4 Fe1 168.86(17) . . ?
O1 C1 C2 119.76(17) . . ?
O1 C1 C6 122.94(17) . . ?
C2 C1 C6 117.28(17) . . ?
O3 C2 C3 118.33(18) . . ?
O3 C2 C1 120.59(17) . . ?
C3 C2 C1 121.06(19) . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.88(19) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 120.55(19) . . ?
C5 C6 C7 118.77(18) . . ?
C1 C6 C7 120.54(17) . . ?
N1 C7 C6 123.55(18) . . ?
N1 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
N1 C8 C9 105.28(16) . . ?
N1 C8 H8A 110.7 . . ?
C9 C8 H8A 110.7 . . ?
N1 C8 H8B 110.7 . . ?
C9 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
N2 C9 C8 111.22(16) . . ?
N2 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N2 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N2 C10 C11 109.92(16) . . ?
N2 C10 H10A 109.7 . . ?
C11 C10 H10A 109.7 . . ?
N2 C10 H10B 109.7 . . ?
C11 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N3 C11 C10 108.93(16) . . ?
N3 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
N3 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N3 C12 C13 126.41(18) . . ?
N3 C12 H12 116.8 . . ?
C13 C12 H12 116.8 . . ?
C18 C13 C14 119.81(19) . . ?
C18 C13 C12 122.49(17) . . ?
C14 C13 C12 117.69(18) . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.32(19) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 120.41(19) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O4 C17 C16 124.95(19) . . ?
O4 C17 C18 114.53(17) . . ?
C16 C17 C18 120.53(19) . . ?
O2 C18 C13 123.19(17) . . ?
O2 C18 C17 118.56(18) . . ?
C13 C18 C17 118.25(17) . . ?
O4 C19 C20 106.67(18) . . ?
O4 C19 H19A 110.4 . . ?
C20 C19 H19A 110.4 . . ?
O4 C19 H19B 110.4 . . ?
C20 C19 H19B 110.4 . . ?
H19A C19 H19B 108.6 . . ?
O3 C21 C22 107.36(17) . . ?
O3 C21 H21A 110.2 . . ?
C22 C21 H21A 110.2 . . ?
O3 C21 H21B 110.2 . . ?
C22 C21 H21B 110.2 . . ?
H21A C21 H21B 108.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C23 S1 178.0(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
Fe1 O1 C1 C2 135.97(15) . . . . ?
Fe1 O1 C1 C6 -45.3(2) . . . . ?
C21 O3 C2 C3 118.12(19) . . . . ?
C21 O3 C2 C1 -63.3(2) . . . . ?
O1 C1 C2 O3 -1.3(3) . . . . ?
C6 C1 C2 O3 179.93(17) . . . . ?
O1 C1 C2 C3 177.23(17) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
O3 C2 C3 C4 177.12(18) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
C2 C3 C4 C5 2.4(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 -2.7(3) . . . . ?
C4 C5 C6 C7 -178.43(19) . . . . ?
O1 C1 C6 C5 -175.19(17) . . . . ?
C2 C1 C6 C5 3.6(3) . . . . ?
O1 C1 C6 C7 0.5(3) . . . . ?
C2 C1 C6 C7 179.26(18) . . . . ?
C8 N1 C7 C6 -169.50(18) . . . . ?
Fe1 N1 C7 C6 2.0(3) . . . . ?
C5 C6 C7 N1 -163.04(19) . . . . ?
C1 C6 C7 N1 21.2(3) . . . . ?
C7 N1 C8 C9 122.60(19) . . . . ?
Fe1 N1 C8 C9 -49.82(18) . . . . ?
C10 N2 C9 C8 97.79(19) . . . . ?
Fe1 N2 C9 C8 -24.24(19) . . . . ?
N1 C8 C9 N2 46.7(2) . . . . ?
C9 N2 C10 C11 -75.5(2) . . . . ?
Fe1 N2 C10 C11 48.68(18) . . . . ?
C12 N3 C11 C10 -158.46(17) . . . . ?
Fe1 N3 C11 C10 18.3(2) . . . . ?
N2 C10 C11 N3 -44.2(2) . . . . ?
C11 N3 C12 C13 178.88(18) . . . . ?
Fe1 N3 C12 C13 2.5(3) . . . . ?
N3 C12 C13 C18 0.9(3) . . . . ?
N3 C12 C13 C14 -177.94(19) . . . . ?
C18 C13 C14 C15 0.2(3) . . . . ?
C12 C13 C14 C15 179.09(19) . . . . ?
C13 C14 C15 C16 1.4(3) . . . . ?
C14 C15 C16 C17 -2.0(3) . . . . ?
C19 O4 C17 C16 0.2(3) . . . . ?
C19 O4 C17 C18 -179.51(17) . . . . ?
C15 C16 C17 O4 -178.80(19) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
Fe1 O2 C18 C13 -5.2(3) . . . . ?
Fe1 O2 C18 C17 174.84(13) . . . . ?
C14 C13 C18 O2 178.70(18) . . . . ?
C12 C13 C18 O2 -0.1(3) . . . . ?
C14 C13 C18 C17 -1.3(3) . . . . ?
C12 C13 C18 C17 179.91(17) . . . . ?
O4 C17 C18 O2 0.5(3) . . . . ?
C16 C17 C18 O2 -179.25(18) . . . . ?
O4 C17 C18 C13 -179.54(17) . . . . ?
C16 C17 C18 C13 0.7(3) . . . . ?
C17 O4 C19 C20 177.97(18) . . . . ?
C2 O3 C21 C22 -144.77(17) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3

_database_code_depnum_ccdc_archive 'CCDC 995963'
