# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 943182'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H31 Fe N5 O3 S'
_chemical_formula_weight         609.52

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2159(4)
_cell_length_b                   10.6166(5)
_cell_length_c                   13.0796(5)
_cell_angle_alpha                83.965(4)
_cell_angle_beta                 87.370(3)
_cell_angle_gamma                89.972(4)
_cell_volume                     1409.23(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7181
_cell_measurement_theta_min      3.0335
_cell_measurement_theta_max      33.3692

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             636
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98329
_exptl_absorpt_correction_T_max  1.00000
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       
;
Rotation method data acquisition using omega and phi scans
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13465
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4943
_reflns_number_gt                3623
_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)+(0.0599P)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         4943
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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
C1 C 0.6823(3) 0.4501(2) 0.1874(2) 0.0206(6) Uani 1 1 d . . .
C2 C 0.5517(3) 0.4662(2) 0.1548(2) 0.0247(6) Uani 1 1 d . . .
H2 H 0.4890 0.4007 0.1735 0.030 Uiso 1 1 calc R . .
C3 C 0.5150(3) 0.5734(3) 0.0975(2) 0.0255(6) Uani 1 1 d . . .
H3 H 0.4273 0.5811 0.0764 0.031 Uiso 1 1 calc R . .
C4 C 0.6048(3) 0.6741(2) 0.06822(19) 0.0211(6) Uani 1 1 d . . .
C5 C 0.5642(3) 0.7860(2) 0.0098(2) 0.0240(6) Uani 1 1 d . . .
H5 H 0.4778 0.7913 -0.0141 0.029 Uiso 1 1 calc R . .
C6 C 0.6483(3) 0.8868(2) -0.0125(2) 0.0255(7) Uani 1 1 d . . .
H6 H 0.6203 0.9617 -0.0514 0.031 Uiso 1 1 calc R . .
C7 C 0.7751(3) 0.8783(2) 0.0224(2) 0.0245(6) Uani 1 1 d . . .
H7 H 0.8325 0.9491 0.0086 0.029 Uiso 1 1 calc R . .
C8 C 0.8185(3) 0.7697(2) 0.07631(19) 0.0222(6) Uani 1 1 d . . .
H8 H 0.9062 0.7657 0.0976 0.027 Uiso 1 1 calc R . .
C9 C 0.7348(3) 0.6631(2) 0.10081(19) 0.0192(6) Uani 1 1 d . . .
C10 C 0.7758(3) 0.5465(2) 0.15834(19) 0.0176(6) Uani 1 1 d . . .
C11 C 0.9100(3) 0.5334(2) 0.18453(19) 0.0207(6) Uani 1 1 d . . .
H11 H 0.9661 0.6040 0.1646 0.025 Uiso 1 1 calc R . .
C12 C 1.1012(3) 0.4362(3) 0.2528(2) 0.0327(7) Uani 1 1 d . . .
H12A H 1.1132 0.4457 0.3263 0.039 Uiso 1 1 calc R . .
H12B H 1.1454 0.5080 0.2105 0.039 Uiso 1 1 calc R . .
C13 C 1.1590(3) 0.3113(3) 0.2254(2) 0.0324(7) Uani 1 1 d . . .
H13A H 1.1579 0.3073 0.1501 0.039 Uiso 1 1 calc R . .
H13B H 1.2509 0.3040 0.2460 0.039 Uiso 1 1 calc R . .
C14 C 1.1150(3) 0.0839(3) 0.2420(2) 0.0285(7) Uani 1 1 d . . .
H14A H 1.2099 0.0695 0.2502 0.034 Uiso 1 1 calc R . .
H14B H 1.0992 0.0893 0.1676 0.034 Uiso 1 1 calc R . .
C15 C 1.0402(3) -0.0289(2) 0.2962(2) 0.0270(7) Uani 1 1 d . . .
H15A H 1.0551 -0.0334 0.3708 0.032 Uiso 1 1 calc R . .
H15B H 1.0766 -0.1069 0.2710 0.032 Uiso 1 1 calc R . .
C16 C 0.8933(3) -0.0267(2) 0.2818(2) 0.0221(6) Uani 1 1 d . . .
H16A H 0.8764 -0.0121 0.2076 0.026 Uiso 1 1 calc R . .
H16B H 0.8542 -0.1094 0.3094 0.026 Uiso 1 1 calc R . .
C17 C 0.7748(2) 0.0408(2) 0.42409(19) 0.0183(6) Uani 1 1 d . . .
H17 H 0.7602 -0.0474 0.4411 0.022 Uiso 1 1 calc R . .
C18 C 0.7296(2) 0.1221(2) 0.49903(19) 0.0188(6) Uani 1 1 d . . .
C19 C 0.6452(3) 0.0723(2) 0.58575(19) 0.0204(6) Uani 1 1 d . . .
C20 C 0.5893(3) -0.0500(2) 0.5954(2) 0.0220(6) Uani 1 1 d . . .
H20 H 0.6085 -0.1044 0.5435 0.026 Uiso 1 1 calc R . .
C21 C 0.5076(3) -0.0919(3) 0.6783(2) 0.0267(7) Uani 1 1 d . . .
H21 H 0.4721 -0.1751 0.6835 0.032 Uiso 1 1 calc R . .
C22 C 0.4762(3) -0.0136(3) 0.7550(2) 0.0312(7) Uani 1 1 d . . .
H22 H 0.4188 -0.0431 0.8117 0.037 Uiso 1 1 calc R . .
C23 C 0.5280(3) 0.1046(3) 0.7485(2) 0.0304(7) Uani 1 1 d . . .
H23 H 0.5062 0.1574 0.8011 0.037 Uiso 1 1 calc R . .
C24 C 0.6132(3) 0.1506(3) 0.6655(2) 0.0245(6) Uani 1 1 d . . .
C25 C 0.6692(3) 0.2733(3) 0.6588(2) 0.0284(7) Uani 1 1 d . . .
H25 H 0.6507 0.3247 0.7129 0.034 Uiso 1 1 calc R . .
C26 C 0.7480(3) 0.3192(2) 0.5783(2) 0.0280(7) Uani 1 1 d . . .
H26 H 0.7837 0.4020 0.5770 0.034 Uiso 1 1 calc R . .
C27 C 0.7791(3) 0.2466(2) 0.4947(2) 0.0224(6) Uani 1 1 d . . .
C28 C 0.8476(2) 0.2221(2) 0.0384(2) 0.0191(6) Uani 1 1 d . . .
N1 N 0.9622(2) 0.43482(19) 0.23272(16) 0.0219(5) Uani 1 1 d . . .
N2 N 1.0792(2) 0.20673(19) 0.28029(17) 0.0250(5) Uani 1 1 d . . .
H1N2 H 1.1008 0.2010 0.3489 0.030 Uiso 1 1 calc R . .
N3 N 0.8330(2) 0.07488(18) 0.33613(16) 0.0171(5) Uani 1 1 d . . .
N4 N 0.8757(2) 0.2153(2) 0.12433(17) 0.0232(5) Uani 1 1 d . . .
O1 O 0.70719(17) 0.34578(15) 0.24620(13) 0.0232(4) Uani 1 1 d . . .
O2 O 0.8569(2) 0.29751(16) 0.41945(14) 0.0295(5) Uani 1 1 d . . .
S1 S 0.80815(7) 0.22869(6) -0.08136(5) 0.02440(18) Uani 1 1 d . . .
Fe1 Fe 0.87074(4) 0.26126(3) 0.27553(3) 0.01894(13) Uani 1 1 d . . .
N1S N 0.4110(3) 0.4013(2) 0.4990(2) 0.0441(7) Uani 1 1 d . . .
C2S C 0.4990(3) 0.4288(3) 0.4226(3) 0.0422(8) Uani 1 1 d . . .
H2S H 0.5018 0.3795 0.3659 0.051 Uiso 1 1 calc R . .
C3S C 0.4130(3) 0.4727(3) 0.5768(3) 0.0461(9) Uani 1 1 d . . .
H3S H 0.3520 0.4553 0.6335 0.055 Uiso 1 1 calc R . .
O1S O 0.1695(2) 0.27067(18) 0.49281(15) 0.0390(5) Uani 1 1 d . . .
H1O1 H 0.2493 0.2905 0.4897 0.047 Uiso 1 1 calc R . .
C1S C 0.1019(4) 0.3378(3) 0.5666(3) 0.0526(10) Uani 1 1 d . . .
H1SB H 0.1504 0.3317 0.6299 0.063 Uiso 1 1 calc R . .
H1SA H 0.0142 0.3012 0.5817 0.063 Uiso 1 1 calc R . .
H1SC H 0.0943 0.4269 0.5394 0.063 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.312(3) . ?
C1 C10 1.411(4) . ?
C1 C2 1.425(4) . ?
C2 C3 1.358(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.419(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.415(4) . ?
C4 C5 1.415(4) . ?
C5 C6 1.371(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.372(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.419(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.452(3) . ?
C10 C11 1.432(4) . ?
C11 N1 1.292(3) . ?
C11 H11 0.9500 . ?
C12 N1 1.456(3) . ?
C12 C13 1.522(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.481(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.485(3) . ?
C14 C15 1.514(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.521(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.472(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.288(3) . ?
C17 C18 1.433(4) . ?
C17 H17 0.9500 . ?
C18 C27 1.409(4) . ?
C18 C19 1.447(4) . ?
C19 C20 1.409(4) . ?
C19 C24 1.427(4) . ?
C20 C21 1.374(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.395(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.354(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.407(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.416(4) . ?
C25 C26 1.345(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.427(4) . ?
C26 H26 0.9500 . ?
C27 O2 1.308(3) . ?
C28 N4 1.168(3) . ?
C28 S1 1.630(3) . ?
N1 Fe1 2.078(2) . ?
N2 Fe1 2.209(2) . ?
N2 H1N2 0.9300 . ?
N3 Fe1 2.082(2) . ?
N4 Fe1 2.085(2) . ?
O1 Fe1 1.9311(17) . ?
O2 Fe1 1.9594(18) . ?
N1S C2S 1.322(4) . ?
N1S C3S 1.332(4) . ?
C2S C3S 1.381(5) 2_666 ?
C2S H2S 0.9500 . ?
C3S C2S 1.381(5) 2_666 ?
C3S H3S 0.9500 . ?
O1S C1S 1.414(4) . ?
O1S H1O1 0.8400 . ?
C1S H1SB 0.9800 . ?
C1S H1SA 0.9800 . ?
C1S H1SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C10 123.7(2) . . ?
O1 C1 C2 116.9(2) . . ?
C10 C1 C2 119.4(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 121.5(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C9 C4 C5 120.2(2) . . ?
C9 C4 C3 119.1(2) . . ?
C5 C4 C3 120.7(2) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 121.1(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C4 C9 C8 117.3(2) . . ?
C4 C9 C10 119.4(2) . . ?
C8 C9 C10 123.3(2) . . ?
C1 C10 C11 122.0(2) . . ?
C1 C10 C9 119.2(2) . . ?
C11 C10 C9 118.8(2) . . ?
N1 C11 C10 126.2(2) . . ?
N1 C11 H11 116.9 . . ?
C10 C11 H11 116.9 . . ?
N1 C12 C13 107.6(2) . . ?
N1 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
N1 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
N2 C13 C12 108.3(2) . . ?
N2 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
N2 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.4 . . ?
N2 C14 C15 114.2(2) . . ?
N2 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
N2 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 114.9(2) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
N3 C16 C15 109.6(2) . . ?
N3 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N3 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
N3 C17 C18 126.8(2) . . ?
N3 C17 H17 116.6 . . ?
C18 C17 H17 116.6 . . ?
C27 C18 C17 119.9(2) . . ?
C27 C18 C19 119.7(2) . . ?
C17 C18 C19 120.0(2) . . ?
C20 C19 C24 117.3(2) . . ?
C20 C19 C18 123.5(2) . . ?
C24 C19 C18 119.2(2) . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 121.3(3) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C25 121.6(2) . . ?
C23 C24 C19 119.7(3) . . ?
C25 C24 C19 118.7(3) . . ?
C26 C25 C24 121.9(3) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C27 121.6(3) . . ?
C25 C26 H26 119.2 . . ?
C27 C26 H26 119.2 . . ?
O2 C27 C18 123.2(2) . . ?
O2 C27 C26 117.9(2) . . ?
C18 C27 C26 118.8(2) . . ?
N4 C28 S1 178.9(2) . . ?
C11 N1 C12 119.5(2) . . ?
C11 N1 Fe1 126.23(18) . . ?
C12 N1 Fe1 114.03(16) . . ?
C13 N2 C14 110.8(2) . . ?
C13 N2 Fe1 108.39(15) . . ?
C14 N2 Fe1 116.73(16) . . ?
C13 N2 H1N2 106.8 . . ?
C14 N2 H1N2 106.8 . . ?
Fe1 N2 H1N2 106.8 . . ?
C17 N3 C16 116.5(2) . . ?
C17 N3 Fe1 125.21(17) . . ?
C16 N3 Fe1 117.74(16) . . ?
C28 N4 Fe1 156.9(2) . . ?
C1 O1 Fe1 130.90(16) . . ?
C27 O2 Fe1 129.03(17) . . ?
O1 Fe1 O2 91.84(8) . . ?
O1 Fe1 N1 87.07(8) . . ?
O2 Fe1 N1 90.71(8) . . ?
O1 Fe1 N3 109.37(8) . . ?
O2 Fe1 N3 84.56(8) . . ?
N1 Fe1 N3 162.98(8) . . ?
O1 Fe1 N4 86.88(8) . . ?
O2 Fe1 N4 176.52(8) . . ?
N1 Fe1 N4 92.45(8) . . ?
N3 Fe1 N4 92.82(8) . . ?
O1 Fe1 N2 164.68(7) . . ?
O2 Fe1 N2 94.42(9) . . ?
N1 Fe1 N2 78.90(8) . . ?
N3 Fe1 N2 85.17(8) . . ?
N4 Fe1 N2 87.61(9) . . ?
C2S N1S C3S 116.5(3) . . ?
N1S C2S C3S 121.6(3) . 2_666 ?
N1S C2S H2S 119.2 . . ?
C3S C2S H2S 119.2 2_666 . ?
N1S C3S C2S 122.0(3) . 2_666 ?
N1S C3S H3S 119.0 . . ?
C2S C3S H3S 119.0 2_666 . ?
C1S O1S H1O1 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
H1SB C1S H1SA 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N2 O1S 0.93 2.24 3.110(3) 156.4 1_655
O1S H1O1 N1S 0.84 2.04 2.839(3) 157.7 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.067
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1c
_database_code_depnum_ccdc_archive 'CCDC 943183'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H33 Fe N4 O3 S'
_chemical_formula_weight         609.53

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2135(3)
_cell_length_b                   10.9173(3)
_cell_length_c                   13.0351(3)
_cell_angle_alpha                98.967(2)
_cell_angle_beta                 93.341(2)
_cell_angle_gamma                90.673(2)
_cell_volume                     1432.94(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11503
_cell_measurement_theta_min      3.0491
_cell_measurement_theta_max      33.3381

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             638
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7838
_exptl_absorpt_correction_T_max  0.8411
_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       
;
Rotation method data acquisition using omega and phi scans
;
_diffrn_detector_area_resol_mean 8.3611
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13158
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0218
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5027
_reflns_number_gt                4287
_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)+(0.0480P)²+0.4360P] 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         5027
_refine_ls_number_parameters     405
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0814
_refine_ls_wR_factor_gt          0.0789
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.81493(17) 0.55314(16) 0.68821(13) 0.0201(4) Uani 1 1 d . . .
C2 C 0.94710(18) 0.53653(18) 0.65956(14) 0.0239(4) Uani 1 1 d . . .
H2 H 1.0106 0.6006 0.6828 0.029 Uiso 1 1 calc R . .
C1SA C 0.8010(6) 0.3237(4) 1.0095(4) 0.0295(15) Uani 0.489(8) 1 d PD A 1
C1SB C 0.7220(5) 0.3234(3) 0.9704(4) 0.0210(13) Uani 0.511(8) 1 d PD A 2
C3 C 0.98359(18) 0.43075(18) 0.59974(14) 0.0246(4) Uani 1 1 d . . .
H3 H 1.0712 0.4241 0.5791 0.030 Uiso 1 1 calc R . .
C2SA C 0.7548(5) 0.3601(4) 0.9094(4) 0.0388(18) Uani 0.489(8) 1 d PD A 1
H2S1 H 0.7888 0.4446 0.9060 0.047 Uiso 0.489(8) 1 calc PR A 1
H2S2 H 0.7905 0.3027 0.8518 0.047 Uiso 0.489(8) 1 calc PR A 1
C2SB C 0.8586(5) 0.3664(5) 0.9603(4) 0.0433(18) Uani 0.511(8) 1 d PD A 2
H2S3 H 0.8962 0.3122 0.9016 0.052 Uiso 0.511(8) 1 calc PR A 2
H2S4 H 0.8565 0.4516 0.9431 0.052 Uiso 0.511(8) 1 calc PR A 2
C4 C 0.89435(18) 0.33012(17) 0.56736(13) 0.0221(4) Uani 1 1 d . . .
C3SA C 0.6109(8) 0.3584(10) 0.8952(9) 0.028(2) Uani 0.489(8) 1 d PD A 1
H3S1 H 0.5741 0.2983 0.9348 0.043 Uiso 0.489(8) 1 calc PR A 1
H3S2 H 0.5844 0.3347 0.8212 0.043 Uiso 0.489(8) 1 calc PR A 1
H3S3 H 0.5782 0.4411 0.9202 0.043 Uiso 0.489(8) 1 calc PR A 1
C3SB C 0.9452(8) 0.3664(8) 1.0548(7) 0.028(2) Uani 0.511(8) 1 d PD A 2
H3S4 H 0.9170 0.4298 1.1104 0.043 Uiso 0.511(8) 1 calc PR A 2
H3S5 H 1.0357 0.3845 1.0399 0.043 Uiso 0.511(8) 1 calc PR A 2
H3S6 H 0.9404 0.2847 1.0769 0.043 Uiso 0.511(8) 1 calc PR A 2
C5 C 0.93461(19) 0.21766(18) 0.50912(14) 0.0254(4) Uani 1 1 d . . .
H5 H 1.0203 0.2127 0.4844 0.030 Uiso 1 1 calc R . .
C6 C 0.85250(19) 0.11675(18) 0.48813(14) 0.0269(4) Uani 1 1 d . . .
H6 H 0.8806 0.0421 0.4488 0.032 Uiso 1 1 calc R . .
C7 C 0.72678(19) 0.12363(17) 0.52474(14) 0.0251(4) Uani 1 1 d . . .
H7 H 0.6712 0.0518 0.5134 0.030 Uiso 1 1 calc R . .
C8 C 0.68183(18) 0.23314(16) 0.57723(14) 0.0219(4) Uani 1 1 d . . .
H8 H 0.5948 0.2365 0.5994 0.026 Uiso 1 1 calc R . .
C9 C 0.76375(17) 0.34048(16) 0.59838(13) 0.0195(4) Uani 1 1 d . . .
C10 C 0.72116(17) 0.45814(16) 0.65320(13) 0.0186(4) Uani 1 1 d . . .
C11 C 0.58416(17) 0.47305(16) 0.66920(13) 0.0199(4) Uani 1 1 d . . .
H11 H 0.5275 0.4041 0.6434 0.024 Uiso 1 1 calc R . .
C12 C 0.38870(17) 0.57157(17) 0.72592(15) 0.0243(4) Uani 1 1 d . . .
H12A H 0.3690 0.5594 0.7972 0.029 Uiso 1 1 calc R . .
H12B H 0.3456 0.5034 0.6759 0.029 Uiso 1 1 calc R . .
C13 C 0.33870(18) 0.69543(17) 0.70408(15) 0.0240(4) Uani 1 1 d . . .
H13A H 0.3447 0.7012 0.6295 0.029 Uiso 1 1 calc R . .
H13B H 0.2456 0.7038 0.7209 0.029 Uiso 1 1 calc R . .
C14 C 0.38849(18) 0.91762(16) 0.73737(14) 0.0222(4) Uani 1 1 d . . .
H14A H 0.2936 0.9322 0.7436 0.027 Uiso 1 1 calc R . .
H14B H 0.4068 0.9145 0.6633 0.027 Uiso 1 1 calc R . .
C15 C 0.46502(18) 1.02595(17) 0.80109(14) 0.0231(4) Uani 1 1 d . . .
H15A H 0.4468 1.0287 0.8752 0.028 Uiso 1 1 calc R . .
H15B H 0.4327 1.1037 0.7793 0.028 Uiso 1 1 calc R . .
C16 C 0.61306(18) 1.02170(16) 0.79164(14) 0.0211(4) Uani 1 1 d . . .
H16A H 0.6327 1.0092 0.7173 0.025 Uiso 1 1 calc R . .
H16B H 0.6542 1.1015 0.8256 0.025 Uiso 1 1 calc R . .
C17 C 0.72777(16) 0.94971(16) 0.93161(13) 0.0184(4) Uani 1 1 d . . .
H17 H 0.7477 1.0353 0.9538 0.022 Uiso 1 1 calc R . .
C18 C 0.76769(17) 0.86647(16) 1.00199(13) 0.0194(4) Uani 1 1 d . . .
C19 C 0.85543(17) 0.91050(17) 1.09133(13) 0.0201(4) Uani 1 1 d . . .
C20 C 0.91968(18) 1.02789(17) 1.10688(14) 0.0226(4) Uani 1 1 d . . .
H20 H 0.9043 1.0818 1.0571 0.027 Uiso 1 1 calc R . .
C21 C 1.00396(18) 1.06585(19) 1.19248(14) 0.0260(4) Uani 1 1 d . . .
H21 H 1.0444 1.1459 1.2017 0.031 Uiso 1 1 calc R . .
C22 C 1.03058(19) 0.98755(19) 1.26598(15) 0.0297(5) Uani 1 1 d . . .
H22 H 1.0903 1.0134 1.3242 0.036 Uiso 1 1 calc R . .
C23 C 0.9703(2) 0.87399(19) 1.25343(14) 0.0296(5) Uani 1 1 d . . .
H23 H 0.9886 0.8209 1.3034 0.035 Uiso 1 1 calc R . .
C24 C 0.88106(18) 0.83330(17) 1.16768(14) 0.0241(4) Uani 1 1 d . . .
C25 C 0.8155(2) 0.71616(18) 1.15576(14) 0.0271(4) Uani 1 1 d . . .
H25 H 0.8306 0.6649 1.2077 0.033 Uiso 1 1 calc R . .
C26 C 0.73231(19) 0.67531(17) 1.07266(15) 0.0257(4) Uani 1 1 d . . .
H26 H 0.6895 0.5967 1.0680 0.031 Uiso 1 1 calc R . .
C27 C 0.70731(18) 0.74820(16) 0.99130(14) 0.0204(4) Uani 1 1 d . . .
C28 C 0.65561(17) 0.78228(16) 0.53639(15) 0.0209(4) Uani 1 1 d . . .
N1 N 0.53066(14) 0.57138(13) 0.71535(11) 0.0196(3) Uani 1 1 d . . .
N2 N 0.41943(14) 0.79566(13) 0.76874(11) 0.0190(3) Uani 1 1 d . . .
H1N2 H 0.3939 0.7994 0.8365 0.023 Uiso 1 1 calc R . .
N3 N 0.66752(14) 0.91984(13) 0.84128(11) 0.0179(3) Uani 1 1 d . . .
N4 N 0.62982(15) 0.78669(14) 0.62144(12) 0.0220(3) Uani 1 1 d . . .
O1 O 0.78880(12) 0.65776(11) 0.74653(10) 0.0234(3) Uani 1 1 d . . .
O1S O 0.7146(2) 0.26351(16) 1.04663(14) 0.0598(5) Uani 1 1 d . . .
O2 O 0.62597(12) 0.70315(11) 0.91327(10) 0.0234(3) Uani 1 1 d . . .
S1 S 0.69203(5) 0.77917(4) 0.41551(4) 0.02506(13) Uani 1 1 d . . .
Fe1 Fe 0.62491(2) 0.73933(2) 0.770550(19) 0.01809(9) Uani 1 1 d . . .
C4SB C 0.6161(14) 0.3558(13) 0.8931(10) 0.068(4) Uani 0.511(8) 1 d PD A 2
H4S1 H 0.5338 0.3130 0.9025 0.101 Uiso 0.511(8) 1 calc PR A 2
H4S2 H 0.6428 0.3296 0.8221 0.101 Uiso 0.511(8) 1 calc PR A 2
H4S3 H 0.6034 0.4456 0.9047 0.101 Uiso 0.511(8) 1 calc PR A 2
C4SA C 0.9404(13) 0.3662(14) 1.0517(14) 0.087(5) Uani 0.489(8) 1 d PD A 1
H4S4 H 0.9433 0.4566 1.0717 0.131 Uiso 0.489(8) 1 calc PR A 1
H4S5 H 1.0021 0.3422 0.9977 0.131 Uiso 0.489(8) 1 calc PR A 1
H4S6 H 0.9647 0.3270 1.1126 0.131 Uiso 0.489(8) 1 calc PR 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
C1 O1 1.309(2) . ?
C1 C10 1.407(3) . ?
C1 C2 1.428(3) . ?
C2 C3 1.358(3) . ?
C2 H2 0.9500 . ?
C1SA O1S 1.257(6) . ?
C1SA C2SA 1.477(8) . ?
C1SA C4SA 1.536(13) . ?
C1SB O1S 1.276(5) . ?
C1SB C2SB 1.487(7) . ?
C1SB C4SB 1.518(12) . ?
C3 C4 1.415(3) . ?
C3 H3 0.9500 . ?
C2SA C3SA 1.470(9) . ?
C2SA H2S1 0.9900 . ?
C2SA H2S2 0.9900 . ?
C2SB C3SB 1.474(9) . ?
C2SB H2S3 0.9900 . ?
C2SB H2S4 0.9900 . ?
C4 C9 1.417(3) . ?
C4 C5 1.418(3) . ?
C3SA H3S1 0.9800 . ?
C3SA H3S2 0.9800 . ?
C3SA H3S3 0.9800 . ?
C3SB H3S4 0.9800 . ?
C3SB H3S5 0.9800 . ?
C3SB H3S6 0.9800 . ?
C5 C6 1.360(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.414(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.454(2) . ?
C10 C11 1.434(2) . ?
C11 N1 1.290(2) . ?
C11 H11 0.9500 . ?
C12 N1 1.464(2) . ?
C12 C13 1.513(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.483(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.485(2) . ?
C14 C15 1.515(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.525(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.470(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.289(2) . ?
C17 C18 1.435(2) . ?
C17 H17 0.9500 . ?
C18 C27 1.408(3) . ?
C18 C19 1.444(3) . ?
C19 C20 1.414(3) . ?
C19 C24 1.416(3) . ?
C20 C21 1.376(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.397(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.360(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.412(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.419(3) . ?
C25 C26 1.352(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.435(3) . ?
C26 H26 0.9500 . ?
C27 O2 1.305(2) . ?
C28 N4 1.148(2) . ?
C28 S1 1.635(2) . ?
N1 Fe1 2.0672(15) . ?
N2 Fe1 2.1937(14) . ?
N2 H1N2 0.9300 . ?
N3 Fe1 2.0712(15) . ?
N4 Fe1 2.0908(16) . ?
O1 Fe1 1.9241(12) . ?
O2 Fe1 1.9606(12) . ?
C4SB H4S1 0.9800 . ?
C4SB H4S2 0.9800 . ?
C4SB H4S3 0.9800 . ?
C4SA H4S4 0.9800 . ?
C4SA H4S5 0.9800 . ?
C4SA H4S6 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C10 123.89(16) . . ?
O1 C1 C2 116.97(16) . . ?
C10 C1 C2 119.15(16) . . ?
C3 C2 C1 121.16(17) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
O1S C1SA C2SA 111.9(6) . . ?
O1S C1SA C4SA 131.2(7) . . ?
C2SA C1SA C4SA 116.9(8) . . ?
O1S C1SB C2SB 111.7(5) . . ?
O1S C1SB C4SB 130.5(7) . . ?
C2SB C1SB C4SB 117.8(8) . . ?
C2 C3 C4 121.66(17) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3SA C2SA C1SA 112.3(6) . . ?
C3SA C2SA H2S1 109.1 . . ?
C1SA C2SA H2S1 109.1 . . ?
C3SA C2SA H2S2 109.1 . . ?
C1SA C2SA H2S2 109.1 . . ?
H2S1 C2SA H2S2 107.9 . . ?
C3SB C2SB C1SB 113.7(6) . . ?
C3SB C2SB H2S3 108.8 . . ?
C1SB C2SB H2S3 108.8 . . ?
C3SB C2SB H2S4 108.8 . . ?
C1SB C2SB H2S4 108.8 . . ?
H2S3 C2SB H2S4 107.7 . . ?
C3 C4 C9 118.94(16) . . ?
C3 C4 C5 121.40(17) . . ?
C9 C4 C5 119.59(17) . . ?
C2SB C3SB H3S4 109.5 . . ?
C2SB C3SB H3S5 109.5 . . ?
H3S4 C3SB H3S5 109.5 . . ?
C2SB C3SB H3S6 109.5 . . ?
H3S4 C3SB H3S6 109.5 . . ?
H3S5 C3SB H3S6 109.5 . . ?
C6 C5 C4 121.08(18) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 119.57(17) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.02(18) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C9 120.77(17) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 117.72(16) . . ?
C8 C9 C10 122.96(16) . . ?
C4 C9 C10 119.28(16) . . ?
C1 C10 C11 122.38(16) . . ?
C1 C10 C9 119.19(16) . . ?
C11 C10 C9 118.43(16) . . ?
N1 C11 C10 126.07(16) . . ?
N1 C11 H11 117.0 . . ?
C10 C11 H11 117.0 . . ?
N1 C12 C13 107.82(14) . . ?
N1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.5 . . ?
N2 C13 C12 108.77(15) . . ?
N2 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N2 C14 C15 114.05(14) . . ?
N2 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
N2 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 114.70(15) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
N3 C16 C15 109.90(14) . . ?
N3 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N3 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N3 C17 C18 126.45(16) . . ?
N3 C17 H17 116.8 . . ?
C18 C17 H17 116.8 . . ?
C27 C18 C17 119.51(16) . . ?
C27 C18 C19 120.27(16) . . ?
C17 C18 C19 119.65(16) . . ?
C20 C19 C24 117.28(17) . . ?
C20 C19 C18 123.29(16) . . ?
C24 C19 C18 119.43(17) . . ?
C21 C20 C19 121.53(18) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 120.55(19) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.42(18) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.45(18) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C19 119.75(18) . . ?
C23 C24 C25 121.57(17) . . ?
C19 C24 C25 118.68(17) . . ?
C26 C25 C24 121.93(17) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C27 121.35(18) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
O2 C27 C18 123.51(16) . . ?
O2 C27 C26 118.17(16) . . ?
C18 C27 C26 118.27(17) . . ?
N4 C28 S1 178.79(16) . . ?
C11 N1 C12 119.41(15) . . ?
C11 N1 Fe1 126.12(12) . . ?
C12 N1 Fe1 114.35(11) . . ?
C13 N2 C14 110.55(14) . . ?
C13 N2 Fe1 108.44(10) . . ?
C14 N2 Fe1 117.82(11) . . ?
C13 N2 H1N2 106.5 . . ?
C14 N2 H1N2 106.5 . . ?
Fe1 N2 H1N2 106.5 . . ?
C17 N3 C16 116.89(15) . . ?
C17 N3 Fe1 124.39(12) . . ?
C16 N3 Fe1 118.34(11) . . ?
C28 N4 Fe1 159.53(14) . . ?
C1 O1 Fe1 130.77(11) . . ?
C1SA O1S C1SB 43.0(3) . . ?
C27 O2 Fe1 127.01(11) . . ?
O1 Fe1 O2 92.24(5) . . ?
O1 Fe1 N1 88.04(5) . . ?
O2 Fe1 N1 90.52(5) . . ?
O1 Fe1 N3 107.64(5) . . ?
O2 Fe1 N3 84.62(5) . . ?
N1 Fe1 N3 163.72(6) . . ?
O1 Fe1 N4 87.60(6) . . ?
O2 Fe1 N4 176.88(6) . . ?
N1 Fe1 N4 92.59(6) . . ?
N3 Fe1 N4 92.46(6) . . ?
O1 Fe1 N2 166.06(5) . . ?
O2 Fe1 N2 93.62(5) . . ?
N1 Fe1 N2 79.27(6) . . ?
N3 Fe1 N2 85.52(5) . . ?
N4 Fe1 N2 87.23(6) . . ?
C1SB C4SB H4S1 109.5 . . ?
C1SB C4SB H4S2 109.5 . . ?
H4S1 C4SB H4S2 109.5 . . ?
C1SB C4SB H4S3 109.5 . . ?
H4S1 C4SB H4S3 109.5 . . ?
H4S2 C4SB H4S3 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N2 O1s 0.93 2.13 2.988(2) 153.5 2_667

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.052
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d_298K
_database_code_depnum_ccdc_archive 'CCDC 943184'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H32 Fe1 N5 O3 S1'
_chemical_formula_weight         610.53

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2153(6)
_cell_length_b                   11.1783(6)
_cell_length_c                   13.2477(6)
_cell_angle_alpha                100.939(4)
_cell_angle_beta                 93.011(4)
_cell_angle_gamma                93.339(4)
_cell_volume                     1479.62(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6597
_cell_measurement_theta_min      2.9452
_cell_measurement_theta_max      33.3869

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             638
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94063
_exptl_absorpt_correction_T_max  1.00000
_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      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_measurement_method       
;
Rotation method data acquisition using omega and phi scans
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14145
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0428
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5205
_reflns_number_gt                3471
_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)+(0.0911P)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         5205
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1500
_refine_ls_wR_factor_gt          0.1416
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8126(3) 0.5617(3) 0.1857(3) 0.0511(8) Uani 1 1 d . . .
C1S C 0.8730(7) 0.4157(6) 0.3877(6) 0.1511(14) Uani 1 1 d . . .
H1S1 H 0.9527 0.4364 0.4309 0.227 Uiso 1 1 calc R . .
H1S2 H 0.8403 0.4886 0.3704 0.227 Uiso 1 1 calc R . .
H1S3 H 0.8904 0.3605 0.3258 0.227 Uiso 1 1 calc R . .
C2 C 0.9464(3) 0.5477(3) 0.1613(3) 0.0626(9) Uani 1 1 d . . .
H2 H 1.0091 0.6122 0.1842 0.075 Uiso 1 1 calc R . .
C2S C 0.6471(7) 0.3653(6) 0.4015(6) 0.1511(14) Uani 1 1 d . . .
H2S1 H 0.6355 0.3177 0.3329 0.227 Uiso 1 1 calc R . .
H2S2 H 0.6316 0.4489 0.4000 0.227 Uiso 1 1 calc R . .
H2S3 H 0.5861 0.3340 0.4444 0.227 Uiso 1 1 calc R . .
C3 C 0.9827(3) 0.4423(4) 0.1057(3) 0.0657(10) Uani 1 1 d . . .
H3 H 1.0692 0.4375 0.0876 0.079 Uiso 1 1 calc R . .
C4 C 0.8941(3) 0.3396(3) 0.0743(2) 0.0565(9) Uani 1 1 d . . .
C3S C 0.8128(8) 0.3141(6) 0.5182(6) 0.1511(14) Uani 1 1 d . . .
H3S H 0.9014 0.3222 0.5403 0.181 Uiso 1 1 calc R . .
C5 C 0.9345(4) 0.2262(4) 0.0203(3) 0.0728(11) Uani 1 1 d . . .
H5 H 1.0201 0.2218 -0.0001 0.087 Uiso 1 1 calc R . .
C6 C 0.8515(5) 0.1257(4) -0.0016(3) 0.0756(11) Uani 1 1 d . . .
H6 H 0.8792 0.0526 -0.0371 0.091 Uiso 1 1 calc R . .
C7 C 0.7252(4) 0.1321(3) 0.0288(3) 0.0693(10) Uani 1 1 d . . .
H7 H 0.6692 0.0616 0.0163 0.083 Uiso 1 1 calc R . .
C8 C 0.6801(4) 0.2395(3) 0.0769(3) 0.0611(9) Uani 1 1 d . . .
H8 H 0.5935 0.2414 0.0953 0.073 Uiso 1 1 calc R . .
C9 C 0.7634(3) 0.3476(3) 0.0989(2) 0.0514(8) Uani 1 1 d . . .
C10 C 0.7198(3) 0.4646(3) 0.1500(2) 0.0488(8) Uani 1 1 d . . .
C11 C 0.5819(3) 0.4756(3) 0.1625(3) 0.0572(9) Uani 1 1 d . . .
H11 H 0.5262 0.4069 0.1358 0.069 Uiso 1 1 calc R . .
C12 C 0.3847(3) 0.5679(3) 0.2115(4) 0.0745(11) Uani 1 1 d . . .
H12A H 0.3601 0.5553 0.2787 0.089 Uiso 1 1 calc R . .
H12B H 0.3435 0.5013 0.1597 0.089 Uiso 1 1 calc R . .
C13 C 0.3403(3) 0.6882(3) 0.1922(3) 0.0706(11) Uani 1 1 d . . .
H13A H 0.3511 0.6940 0.1209 0.085 Uiso 1 1 calc R . .
H13B H 0.2481 0.6939 0.2050 0.085 Uiso 1 1 calc R . .
C14 C 0.3922(4) 0.9083(3) 0.2347(3) 0.0653(10) Uani 1 1 d . . .
H14A H 0.2990 0.9192 0.2388 0.078 Uiso 1 1 calc R . .
H14B H 0.4133 0.9074 0.1640 0.078 Uiso 1 1 calc R . .
C15 C 0.4682(4) 1.0155(3) 0.3036(3) 0.0658(10) Uani 1 1 d . . .
H15A H 0.4475 1.0154 0.3742 0.079 Uiso 1 1 calc R . .
H15B H 0.4383 1.0901 0.2858 0.079 Uiso 1 1 calc R . .
C16 C 0.6164(4) 1.0179(3) 0.2983(3) 0.0600(9) Uani 1 1 d . . .
H16A H 0.6387 1.0090 0.2271 0.072 Uiso 1 1 calc R . .
H16B H 0.6561 1.0956 0.3359 0.072 Uiso 1 1 calc R . .
C17 C 0.7271(3) 0.9474(3) 0.4335(3) 0.0488(8) Uani 1 1 d . . .
H17 H 0.7482 1.0302 0.4583 0.059 Uiso 1 1 calc R . .
C18 C 0.7638(3) 0.8670(3) 0.4994(2) 0.0459(8) Uani 1 1 d . . .
C20 C 0.9194(3) 1.0263(3) 0.6097(3) 0.0612(9) Uani 1 1 d . . .
H20 H 0.9088 1.0780 0.5630 0.073 Uiso 1 1 calc R . .
C21 C 1.0026(4) 1.0642(4) 0.6969(3) 0.0732(11) Uani 1 1 d . . .
H21 H 1.0460 1.1415 0.7089 0.088 Uiso 1 1 calc R . .
C22 C 1.0221(4) 0.9885(5) 0.7665(3) 0.0818(12) Uani 1 1 d . . .
H22 H 1.0804 1.0138 0.8239 0.098 Uiso 1 1 calc R . .
C23 C 0.9563(4) 0.8774(4) 0.7512(3) 0.0762(11) Uani 1 1 d . . .
H23 H 0.9681 0.8278 0.7994 0.091 Uiso 1 1 calc R . .
C25 C 0.8010(4) 0.7206(4) 0.6476(3) 0.0716(11) Uani 1 1 d . . .
H25 H 0.8117 0.6720 0.6968 0.086 Uiso 1 1 calc R . .
C26 C 0.7191(4) 0.6785(3) 0.5627(3) 0.0674(10) Uani 1 1 d . . .
H26 H 0.6745 0.6020 0.5551 0.081 Uiso 1 1 calc R . .
C27 C 0.7003(3) 0.7494(3) 0.4848(3) 0.0520(8) Uani 1 1 d . . .
C28 C 0.6586(3) 0.7856(3) 0.0402(3) 0.0543(9) Uani 1 1 d . . .
N1 N 0.5281(2) 0.5710(2) 0.2070(2) 0.0568(7) Uani 1 1 d . . .
N1S N 0.7769(6) 0.3586(4) 0.4416(4) 0.1139(15) Uani 1 1 d . . .
N2 N 0.4196(3) 0.7886(2) 0.2611(2) 0.0543(7) Uani 1 1 d . . .
H1N2 H 0.3916 0.7902 0.3254 0.065 Uiso 1 1 calc R . .
N3 N 0.6677(2) 0.9181(2) 0.3430(2) 0.0481(6) Uani 1 1 d . . .
N4 N 0.6335(3) 0.7884(3) 0.1225(3) 0.0656(8) Uani 1 1 d . . .
O1 O 0.7863(2) 0.6653(2) 0.2430(2) 0.0640(7) Uani 1 1 d . . .
O1S O 0.7323(4) 0.2588(4) 0.5661(3) 0.1391(15) Uani 1 1 d . . .
O2 O 0.6186(2) 0.70383(19) 0.40568(18) 0.0590(6) Uani 1 1 d . . .
S1 S 0.69384(10) 0.78788(10) -0.07900(8) 0.0750(3) Uani 1 1 d . . .
Fe1 Fe 0.62336(4) 0.74005(4) 0.26656(4) 0.0504(2) Uani 1 1 d . . .
C19 C 0.8502(3) 0.9106(3) 0.5905(2) 0.0500(8) Uani 1 1 d . . .
C24 C 0.8698(3) 0.8354(3) 0.6631(3) 0.0585(9) 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 O1 1.309(4) . ?
C1 C10 1.392(4) . ?
C1 C2 1.431(5) . ?
C1S N1S 1.434(7) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
C2 C3 1.349(5) . ?
C2 H2 0.9300 . ?
C2S N1S 1.413(8) . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
C3 C4 1.403(5) . ?
C3 H3 0.9300 . ?
C4 C9 1.394(5) . ?
C4 C5 1.427(5) . ?
C3S N1S 1.258(8) . ?
C3S O1S 1.268(7) . ?
C3S H3S 0.9300 . ?
C5 C6 1.344(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.366(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.461(4) . ?
C10 C11 1.436(5) . ?
C11 N1 1.285(4) . ?
C11 H11 0.9300 . ?
C12 N1 1.468(4) . ?
C12 C13 1.507(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.476(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.484(4) . ?
C14 C15 1.508(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.518(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N3 1.468(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.291(4) . ?
C17 C18 1.418(4) . ?
C17 H17 0.9300 . ?
C18 C27 1.405(4) . ?
C18 C19 1.446(4) . ?
C20 C21 1.381(5) . ?
C20 C19 1.410(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.379(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.352(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.413(5) . ?
C23 H23 0.9300 . ?
C25 C26 1.357(5) . ?
C25 C24 1.402(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.428(5) . ?
C26 H26 0.9300 . ?
C27 O2 1.308(4) . ?
C28 N4 1.128(4) . ?
C28 S1 1.643(4) . ?
N1 Fe1 2.068(3) . ?
N2 Fe1 2.183(3) . ?
N2 H1N2 0.9100 . ?
N3 Fe1 2.067(2) . ?
N4 Fe1 2.086(3) . ?
O1 Fe1 1.919(2) . ?
O2 Fe1 1.963(2) . ?
C19 C24 1.406(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C10 124.2(3) . . ?
O1 C1 C2 117.1(3) . . ?
C10 C1 C2 118.7(3) . . ?
N1S C1S H1S1 109.5 . . ?
N1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
N1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N1S C2S H2S1 109.5 . . ?
N1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
N1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C2 C3 C4 122.1(3) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C9 C4 C3 119.1(3) . . ?
C9 C4 C5 119.0(3) . . ?
C3 C4 C5 121.9(3) . . ?
N1S C3S O1S 122.2(8) . . ?
N1S C3S H3S 118.9 . . ?
O1S C3S H3S 118.9 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 121.6(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.7(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 117.8(3) . . ?
C4 C9 C10 119.4(3) . . ?
C8 C9 C10 122.7(3) . . ?
C1 C10 C11 122.0(3) . . ?
C1 C10 C9 119.3(3) . . ?
C11 C10 C9 118.7(3) . . ?
N1 C11 C10 126.4(3) . . ?
N1 C11 H11 116.8 . . ?
C10 C11 H11 116.8 . . ?
N1 C12 C13 107.9(3) . . ?
N1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N2 C13 C12 109.1(3) . . ?
N2 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N2 C14 C15 113.7(3) . . ?
N2 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 115.3(3) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
N3 C16 C15 109.8(3) . . ?
N3 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N3 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N3 C17 C18 127.1(3) . . ?
N3 C17 H17 116.5 . . ?
C18 C17 H17 116.5 . . ?
C27 C18 C17 119.5(3) . . ?
C27 C18 C19 119.2(3) . . ?
C17 C18 C19 120.5(3) . . ?
C21 C20 C19 121.0(4) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.6(4) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.0(4) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 121.1(4) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C26 C25 C24 121.7(3) . . ?
C26 C25 H25 119.2 . . ?
C24 C25 H25 119.2 . . ?
C25 C26 C27 121.1(3) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
O2 C27 C18 123.2(3) . . ?
O2 C27 C26 117.9(3) . . ?
C18 C27 C26 118.9(3) . . ?
N4 C28 S1 177.5(3) . . ?
C11 N1 C12 119.6(3) . . ?
C11 N1 Fe1 126.1(2) . . ?
C12 N1 Fe1 114.1(2) . . ?
C3S N1S C2S 127.7(6) . . ?
C3S N1S C1S 119.7(7) . . ?
C2S N1S C1S 112.5(5) . . ?
C13 N2 C14 110.9(3) . . ?
C13 N2 Fe1 108.2(2) . . ?
C14 N2 Fe1 118.0(2) . . ?
C13 N2 H1N2 106.3 . . ?
C14 N2 H1N2 106.3 . . ?
Fe1 N2 H1N2 106.3 . . ?
C17 N3 C16 116.9(3) . . ?
C17 N3 Fe1 123.8(2) . . ?
C16 N3 Fe1 118.9(2) . . ?
C28 N4 Fe1 160.2(3) . . ?
C1 O1 Fe1 131.3(2) . . ?
C27 O2 Fe1 126.59(19) . . ?
O1 Fe1 O2 92.66(11) . . ?
O1 Fe1 N3 107.57(10) . . ?
O2 Fe1 N3 84.43(9) . . ?
O1 Fe1 N1 87.75(10) . . ?
O2 Fe1 N1 89.70(10) . . ?
N3 Fe1 N1 163.79(10) . . ?
O1 Fe1 N4 87.60(12) . . ?
O2 Fe1 N4 176.72(10) . . ?
N3 Fe1 N4 92.37(11) . . ?
N1 Fe1 N4 93.58(12) . . ?
O1 Fe1 N2 165.59(10) . . ?
O2 Fe1 N2 93.92(10) . . ?
N3 Fe1 N2 85.84(10) . . ?
N1 Fe1 N2 79.48(10) . . ?
N4 Fe1 N2 86.57(11) . . ?
C24 C19 C20 117.5(3) . . ?
C24 C19 C18 119.8(3) . . ?
C20 C19 C18 122.6(3) . . ?
C25 C24 C19 119.2(3) . . ?
C25 C24 C23 121.1(4) . . ?
C19 C24 C23 119.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N2 O1S 0.91 2.09 2.944(4) 155.4 2_666

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.978
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.061
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d'_308K
_database_code_depnum_ccdc_archive 'CCDC 943185'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H32 Fe N5 O3 Se'
_chemical_formula_weight         657.43

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2841(3)
_cell_length_b                   11.2785(3)
_cell_length_c                   13.2216(4)
_cell_angle_alpha                101.184(3)
_cell_angle_beta                 93.834(3)
_cell_angle_gamma                92.497(2)
_cell_volume                     1498.57(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    308(2)
_cell_measurement_reflns_used    6226
_cell_measurement_theta_min      2.9422
_cell_measurement_theta_max      33.3442

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             674
_exptl_absorpt_coefficient_mu    1.758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  1.0000
_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      308(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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14216
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5271
_reflns_number_gt                3044
_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)+(0.0705P)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         5271
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1201
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.913
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8132(4) 0.5677(4) 0.1881(3) 0.0521(10) Uani 1 1 d . . .
C1S C 0.8669(7) 0.4178(6) 0.3900(6) 0.1502(15) Uani 1 1 d . A .
H1S1 H 0.9513 0.4187 0.4258 0.225 Uiso 1 1 calc R . .
H1S2 H 0.8441 0.4994 0.3897 0.225 Uiso 1 1 calc R . .
H1S3 H 0.8688 0.3744 0.3201 0.225 Uiso 1 1 calc R . .
C2S C 0.6392(8) 0.3663(6) 0.4002(6) 0.1502(15) Uani 1 1 d . A 1
H2S1 H 0.6281 0.3196 0.3310 0.225 Uiso 1 1 calc R A 1
H2S2 H 0.6237 0.4494 0.3992 0.225 Uiso 1 1 calc R A 1
H2S3 H 0.5783 0.3355 0.4421 0.225 Uiso 1 1 calc R A 1
C4 C 0.8994(4) 0.3488(4) 0.0748(3) 0.0614(11) Uani 1 1 d . . .
C3S C 0.8110(9) 0.3102(7) 0.5177(7) 0.1502(15) Uani 1 1 d . A .
H3S H 0.8997 0.3146 0.5382 0.180 Uiso 1 1 calc R . .
C5 C 0.9405(5) 0.2375(5) 0.0186(3) 0.0760(13) Uani 1 1 d . . .
H5 H 1.0247 0.2343 -0.0031 0.091 Uiso 1 1 calc R . .
C6 C 0.8601(6) 0.1366(5) -0.0036(3) 0.0778(14) Uani 1 1 d . . .
H6 H 0.8891 0.0644 -0.0392 0.093 Uiso 1 1 calc R . .
C7 C 0.7353(5) 0.1415(4) 0.0266(3) 0.0735(13) Uani 1 1 d . . .
H7 H 0.6807 0.0714 0.0132 0.088 Uiso 1 1 calc R . .
C8 C 0.6894(4) 0.2486(4) 0.0764(3) 0.0635(11) Uani 1 1 d . . .
H8 H 0.6039 0.2496 0.0953 0.076 Uiso 1 1 calc R . .
C9 C 0.7687(4) 0.3562(4) 0.0994(3) 0.0539(10) Uani 1 1 d . . .
C10 C 0.7230(4) 0.4714(3) 0.1514(3) 0.0490(9) Uani 1 1 d . . .
C11 C 0.5867(4) 0.4808(4) 0.1635(3) 0.0580(10) Uani 1 1 d . . .
H11 H 0.5327 0.4122 0.1361 0.070 Uiso 1 1 calc R . .
C12 C 0.3891(4) 0.5703(4) 0.2135(4) 0.0752(13) Uani 1 1 d . . .
H12A H 0.3670 0.5584 0.2812 0.090 Uiso 1 1 calc R . .
H12B H 0.3484 0.5036 0.1619 0.090 Uiso 1 1 calc R . .
C13 C 0.3406(4) 0.6892(4) 0.1938(4) 0.0729(12) Uani 1 1 d . . .
H13A H 0.3500 0.6951 0.1224 0.088 Uiso 1 1 calc R . .
H13B H 0.2491 0.6941 0.2066 0.088 Uiso 1 1 calc R . .
C14 C 0.3896(4) 0.9075(4) 0.2379(3) 0.0650(11) Uani 1 1 d . . .
H14A H 0.2970 0.9184 0.2422 0.078 Uiso 1 1 calc R . .
H14B H 0.4092 0.9064 0.1670 0.078 Uiso 1 1 calc R . .
C15 C 0.4647(4) 1.0138(4) 0.3071(3) 0.0689(12) Uani 1 1 d . . .
H15A H 0.4462 1.0134 0.3780 0.083 Uiso 1 1 calc R . .
H15B H 0.4326 1.0876 0.2899 0.083 Uiso 1 1 calc R . .
C16 C 0.6111(4) 1.0176(3) 0.3013(3) 0.0617(11) Uani 1 1 d . . .
H16A H 0.6317 1.0091 0.2298 0.074 Uiso 1 1 calc R . .
H16B H 0.6495 1.0949 0.3392 0.074 Uiso 1 1 calc R . .
C17 C 0.7279(4) 0.9476(3) 0.4362(3) 0.0501(9) Uani 1 1 d . . .
H17 H 0.7494 1.0295 0.4611 0.060 Uiso 1 1 calc R . .
C18 C 0.7668(3) 0.8654(3) 0.5024(3) 0.0471(9) Uani 1 1 d . . .
C19 C 0.8559(4) 0.9096(4) 0.5915(3) 0.0503(9) Uani 1 1 d . . .
C20 C 0.9234(4) 1.0234(4) 0.6112(3) 0.0646(11) Uani 1 1 d . . .
H20 H 0.9108 1.0748 0.5647 0.078 Uiso 1 1 calc R . .
C21 C 1.0085(4) 1.0606(5) 0.6986(4) 0.0773(13) Uani 1 1 d . . .
H21 H 1.0508 1.1371 0.7104 0.093 Uiso 1 1 calc R . .
C22 C 1.0313(5) 0.9864(6) 0.7681(4) 0.0830(14) Uani 1 1 d . . .
H22 H 1.0897 1.0119 0.8259 0.100 Uiso 1 1 calc R . .
C23 C 0.9683(5) 0.8763(5) 0.7518(3) 0.0778(13) Uani 1 1 d . . .
H23 H 0.9840 0.8261 0.7988 0.093 Uiso 1 1 calc R . .
C24 C 0.8783(4) 0.8349(4) 0.6641(3) 0.0594(11) Uani 1 1 d . . .
C25 C 0.8102(4) 0.7220(4) 0.6486(3) 0.0699(12) Uani 1 1 d . . .
H25 H 0.8227 0.6739 0.6977 0.084 Uiso 1 1 calc R . .
C26 C 0.7266(4) 0.6806(4) 0.5645(3) 0.0652(11) Uani 1 1 d . . .
H26 H 0.6832 0.6050 0.5571 0.078 Uiso 1 1 calc R . .
C27 C 0.7040(4) 0.7510(3) 0.4872(3) 0.0505(9) Uani 1 1 d . . .
C28 C 0.6521(4) 0.7900(3) 0.0409(3) 0.0535(10) Uani 1 1 d . . .
N1 N 0.5312(3) 0.5743(3) 0.2084(3) 0.0574(8) Uani 1 1 d . . .
N1S N 0.7696(7) 0.3580(4) 0.4425(4) 0.1140(17) Uani 1 1 d . . .
N2 N 0.4193(3) 0.7890(3) 0.2643(2) 0.0566(8) Uani 1 1 d . . .
H1N2 H 0.3924 0.7904 0.3287 0.068 Uiso 1 1 calc R . .
N3 N 0.6660(3) 0.9186(2) 0.3458(2) 0.0498(8) Uani 1 1 d . . .
N4 N 0.6287(4) 0.7884(3) 0.1241(3) 0.0679(10) Uani 1 1 d . . .
O1 O 0.7856(2) 0.6701(2) 0.2453(2) 0.0642(7) Uani 1 1 d . . .
O1S O 0.7294(5) 0.2566(4) 0.5639(3) 0.1327(16) Uani 1 1 d . . .
O2 O 0.6212(3) 0.7064(2) 0.4083(2) 0.0592(7) Uani 1 1 d . . .
Se1 Se 0.68867(5) 0.79431(4) -0.08798(3) 0.0736(2) Uani 1 1 d . . .
Fe1 Fe 0.62191(5) 0.74172(4) 0.26969(4) 0.05142(19) Uani 1 1 d . . .
C2 C 0.9461(4) 0.5554(4) 0.1643(3) 0.0663(12) Uani 1 1 d . . .
H2 H 1.0069 0.6200 0.1875 0.080 Uiso 1 1 calc R . .
C3 C 0.9842(4) 0.4517(4) 0.1090(3) 0.0687(12) Uani 1 1 d . . .
H3 H 1.0707 0.4480 0.0926 0.082 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.306(4) . ?
C1 C10 1.387(5) . ?
C1 C2 1.429(5) . ?
C1S N1S 1.468(7) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
C2S N1S 1.432(8) . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
C4 C3 1.403(6) . ?
C4 C9 1.406(5) . ?
C4 C5 1.426(6) . ?
C3S O1S 1.269(8) . ?
C3S N1S 1.277(9) . ?
C3S H3S 0.9300 . ?
C5 C6 1.349(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.402(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.460(5) . ?
C10 C11 1.427(5) . ?
C11 N1 1.283(5) . ?
C11 H11 0.9300 . ?
C12 N1 1.468(5) . ?
C12 C13 1.514(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.485(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.485(5) . ?
C14 C15 1.507(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.512(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N3 1.476(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.292(4) . ?
C17 C18 1.444(5) . ?
C17 H17 0.9300 . ?
C18 C27 1.390(5) . ?
C18 C19 1.436(5) . ?
C19 C20 1.401(5) . ?
C19 C24 1.409(5) . ?
C20 C21 1.387(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.374(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.348(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.424(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.399(6) . ?
C25 C26 1.352(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.424(5) . ?
C26 H26 0.9300 . ?
C27 O2 1.306(4) . ?
C28 N4 1.145(5) . ?
C28 Se1 1.779(5) . ?
N1 Fe1 2.060(3) . ?
N2 Fe1 2.173(3) . ?
N2 H1N2 0.9100 . ?
N3 Fe1 2.068(3) . ?
N4 Fe1 2.096(4) . ?
O1 Fe1 1.919(3) . ?
O2 Fe1 1.950(3) . ?
C2 C3 1.343(6) . ?
C2 H2 0.9300 . ?
C3 H3 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
O1 C1 C10 124.3(3) . . ?
O1 C1 C2 116.7(4) . . ?
C10 C1 C2 119.0(4) . . ?
N1S C1S H1S1 109.5 . . ?
N1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
N1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
N1S C2S H2S1 109.5 . . ?
N1S C2S H2S2 109.5 . . ?
N1S C2S H2S3 109.5 . . ?
C3 C4 C9 117.9(4) . . ?
C3 C4 C5 123.0(4) . . ?
C9 C4 C5 119.1(4) . . ?
O1S C3S N1S 119.0(8) . . ?
O1S C3S H3S 120.5 . . ?
N1S C3S H3S 120.5 . . ?
C6 C5 C4 121.5(5) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C9 121.5(4) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C4 117.1(4) . . ?
C8 C9 C10 123.0(4) . . ?
C4 C9 C10 119.8(4) . . ?
C1 C10 C11 122.1(3) . . ?
C1 C10 C9 119.1(3) . . ?
C11 C10 C9 118.8(3) . . ?
N1 C11 C10 126.6(3) . . ?
N1 C11 H11 116.7 . . ?
C10 C11 H11 116.7 . . ?
N1 C12 C13 108.1(3) . . ?
N1 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
N1 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
N2 C13 C12 108.1(3) . . ?
N2 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
N2 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N2 C14 C15 113.7(3) . . ?
N2 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 115.6(3) . . ?
C14 C15 H15A 108.4 . . ?
C16 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C16 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
N3 C16 C15 109.7(3) . . ?
N3 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N3 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N3 C17 C18 126.4(3) . . ?
N3 C17 H17 116.8 . . ?
C18 C17 H17 116.8 . . ?
C27 C18 C19 121.0(3) . . ?
C27 C18 C17 119.4(3) . . ?
C19 C18 C17 119.0(3) . . ?
C20 C19 C24 117.2(4) . . ?
C20 C19 C18 124.0(4) . . ?
C24 C19 C18 118.7(4) . . ?
C21 C20 C19 121.3(4) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 121.1(5) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C21 119.3(5) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C22 C23 C24 121.6(4) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C19 119.0(4) . . ?
C25 C24 C23 121.5(4) . . ?
C19 C24 C23 119.5(4) . . ?
C26 C25 C24 122.1(4) . . ?
C26 C25 H25 118.9 . . ?
C24 C25 H25 118.9 . . ?
C25 C26 C27 121.0(4) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
O2 C27 C18 123.7(3) . . ?
O2 C27 C26 118.1(3) . . ?
C18 C27 C26 118.1(4) . . ?
N4 C28 Se1 179.4(4) . . ?
C11 N1 C12 120.1(3) . . ?
C11 N1 Fe1 126.1(3) . . ?
C12 N1 Fe1 113.7(2) . . ?
C3S N1S C2S 130.3(7) . . ?
C3S N1S C1S 117.5(7) . . ?
C2S N1S C1S 112.2(5) . . ?
C13 N2 C14 110.5(3) . . ?
C13 N2 Fe1 108.4(2) . . ?
C14 N2 Fe1 117.8(2) . . ?
C13 N2 H1N2 106.5 . . ?
C14 N2 H1N2 106.5 . . ?
Fe1 N2 H1N2 106.5 . . ?
C17 N3 C16 117.2(3) . . ?
C17 N3 Fe1 123.6(2) . . ?
C16 N3 Fe1 118.8(2) . . ?
C28 N4 Fe1 162.9(3) . . ?
C1 O1 Fe1 131.2(2) . . ?
C27 O2 Fe1 126.6(2) . . ?
O1 Fe1 O2 93.00(12) . . ?
O1 Fe1 N1 87.84(12) . . ?
O2 Fe1 N1 90.32(12) . . ?
O1 Fe1 N3 106.44(11) . . ?
O2 Fe1 N3 84.74(11) . . ?
N1 Fe1 N3 165.08(12) . . ?
O1 Fe1 N4 86.78(13) . . ?
O2 Fe1 N4 176.89(12) . . ?
N1 Fe1 N4 92.76(13) . . ?
N3 Fe1 N4 92.35(13) . . ?
O1 Fe1 N2 165.85(12) . . ?
O2 Fe1 N2 94.10(12) . . ?
N1 Fe1 N2 79.90(12) . . ?
N3 Fe1 N2 86.40(12) . . ?
N4 Fe1 N2 86.78(13) . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 122.9(4) . . ?
C2 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N2 O1S 0.91 2.08 2.935(5) 155.3 2_666

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.868
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.065
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d_150K
_database_code_depnum_ccdc_archive 'CCDC 1030134'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H25 Fe N4 O2 S, C3 H7 N O'
_chemical_formula_sum            'C31 H32 Fe N5 O3 S'
_chemical_formula_weight         610.53

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2652(3)
_cell_length_b                   11.4487(3)
_cell_length_c                   12.7914(4)
_cell_angle_alpha                106.073(2)
_cell_angle_beta                 92.837(2)
_cell_angle_gamma                97.652(2)
_cell_volume                     1425.77(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5455
_cell_measurement_theta_min      2.9466
_cell_measurement_theta_max      33.3254

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             638
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92313
_exptl_absorpt_correction_T_max  1.00000
_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         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13537
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5015
_reflns_number_gt                4051
_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)+(0.0686P)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         5015
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.79082(18) 0.58769(18) 0.21302(16) 0.0215(4) Uani 1 1 d . . .
C1S C 0.9113(2) 0.4029(3) 0.3766(2) 0.0479(7) Uani 1 1 d . . .
H1S1 H 0.9998 0.4001 0.4026 0.072 Uiso 1 1 calc R . .
H1S2 H 0.8997 0.4869 0.3857 0.072 Uiso 1 1 calc R . .
H1S3 H 0.8955 0.3579 0.3006 0.072 Uiso 1 1 calc R . .
C2 C 0.9256(2) 0.5869(2) 0.18903(17) 0.0281(5) Uani 1 1 d . . .
H2 H 0.9867 0.6577 0.2183 0.034 Uiso 1 1 calc R . .
C2S C 0.6799(2) 0.3497(2) 0.4117(2) 0.0400(6) Uani 1 1 d . . .
H2S1 H 0.6275 0.3079 0.4543 0.060 Uiso 1 1 calc R . .
H2S2 H 0.6567 0.3089 0.3354 0.060 Uiso 1 1 calc R . .
H2S3 H 0.6639 0.4333 0.4277 0.060 Uiso 1 1 calc R . .
C3 C 0.9657(2) 0.4857(2) 0.12495(17) 0.0288(5) Uani 1 1 d . . .
H3 H 1.0528 0.4901 0.1076 0.035 Uiso 1 1 calc R . .
C4 C 0.8791(2) 0.3728(2) 0.08326(16) 0.0264(5) Uani 1 1 d . . .
C3S C 0.8592(2) 0.29395(19) 0.51102(17) 0.0316(5) Uani 1 1 d . . .
H3SA H 0.9495 0.2945 0.5224 0.038 Uiso 1 1 calc R . .
C5 C 0.9231(2) 0.2652(2) 0.02067(17) 0.0320(5) Uani 1 1 d . . .
H5 H 1.0087 0.2699 -0.0001 0.038 Uiso 1 1 calc R . .
C6 C 0.8424(2) 0.1550(2) -0.00968(18) 0.0353(5) Uani 1 1 d . . .
H6 H 0.8728 0.0851 -0.0510 0.042 Uiso 1 1 calc R . .
C7 C 0.7139(2) 0.1471(2) 0.02139(18) 0.0325(5) Uani 1 1 d . . .
H7 H 0.6603 0.0710 0.0037 0.039 Uiso 1 1 calc R . .
C8 C 0.6658(2) 0.25046(18) 0.07766(17) 0.0272(5) Uani 1 1 d . . .
H8 H 0.5789 0.2437 0.0955 0.033 Uiso 1 1 calc R . .
C9 C 0.74585(19) 0.36700(18) 0.10904(16) 0.0232(4) Uani 1 1 d . . .
C10 C 0.69947(18) 0.47913(18) 0.16858(16) 0.0213(4) Uani 1 1 d . . .
C11 C 0.56073(18) 0.47751(18) 0.17718(16) 0.0223(4) Uani 1 1 d . . .
H11 H 0.5061 0.4021 0.1508 0.027 Uiso 1 1 calc R . .
C12 C 0.36211(19) 0.56060(18) 0.22183(18) 0.0275(5) Uani 1 1 d . . .
H12A H 0.3375 0.5516 0.2918 0.033 Uiso 1 1 calc R . .
H12B H 0.3189 0.4892 0.1645 0.033 Uiso 1 1 calc R . .
C13 C 0.32287(19) 0.67673(19) 0.20474(17) 0.0268(5) Uani 1 1 d . . .
H13A H 0.3325 0.6779 0.1299 0.032 Uiso 1 1 calc R . .
H13B H 0.2315 0.6813 0.2191 0.032 Uiso 1 1 calc R . .
C14 C 0.3938(2) 0.89857(18) 0.25674(17) 0.0265(5) Uani 1 1 d . . .
H14A H 0.3031 0.9121 0.2653 0.032 Uiso 1 1 calc R . .
H14B H 0.4092 0.8901 0.1810 0.032 Uiso 1 1 calc R . .
C15 C 0.48471(19) 1.01051(18) 0.32827(17) 0.0260(5) Uani 1 1 d . . .
H15A H 0.4677 1.0200 0.4039 0.031 Uiso 1 1 calc R . .
H15B H 0.4635 1.0828 0.3098 0.031 Uiso 1 1 calc R . .
C16 C 0.63082(19) 1.00513(18) 0.31796(17) 0.0239(4) Uani 1 1 d . . .
H16A H 0.6486 0.9899 0.2420 0.029 Uiso 1 1 calc R . .
H16B H 0.6823 1.0831 0.3592 0.029 Uiso 1 1 calc R . .
C17 C 0.73725(18) 0.93741(17) 0.45337(15) 0.0198(4) Uani 1 1 d . . .
H17 H 0.7755 1.0194 0.4813 0.024 Uiso 1 1 calc R . .
C18 C 0.75922(18) 0.85580(17) 0.51737(15) 0.0190(4) Uani 1 1 d . . .
C19 C 0.85476(18) 0.89636(17) 0.61127(15) 0.0192(4) Uani 1 1 d . . .
C20 C 0.94557(19) 1.00731(18) 0.63534(16) 0.0235(4) Uani 1 1 d . . .
H20 H 0.9445 1.0570 0.5889 0.028 Uiso 1 1 calc R . .
C21 C 1.03496(19) 1.04265(19) 0.72597(16) 0.0260(5) Uani 1 1 d . . .
H21 H 1.0922 1.1166 0.7409 0.031 Uiso 1 1 calc R . .
C22 C 1.0406(2) 0.9686(2) 0.79582(17) 0.0280(5) Uani 1 1 d . . .
H22 H 1.1030 0.9919 0.8559 0.034 Uiso 1 1 calc R . .
C23 C 0.95435(19) 0.8619(2) 0.77552(17) 0.0277(5) Uani 1 1 d . . .
H23 H 0.9578 0.8133 0.8227 0.033 Uiso 1 1 calc R . .
C24 C 0.86020(19) 0.82401(18) 0.68435(16) 0.0229(4) Uani 1 1 d . . .
C25 C 0.7669(2) 0.71476(19) 0.66437(17) 0.0269(5) Uani 1 1 d . . .
H25 H 0.7686 0.6674 0.7128 0.032 Uiso 1 1 calc R . .
C26 C 0.67599(19) 0.67791(18) 0.57715(17) 0.0245(5) Uani 1 1 d . . .
H26 H 0.6160 0.6065 0.5673 0.029 Uiso 1 1 calc R . .
C27 C 0.67039(18) 0.74630(17) 0.50029(15) 0.0204(4) Uani 1 1 d . . .
C28 C 0.65245(18) 0.77574(17) 0.06337(17) 0.0219(4) Uani 1 1 d . . .
N1 N 0.50599(15) 0.57267(15) 0.21876(13) 0.0212(4) Uani 1 1 d . . .
N1S N 0.81859(17) 0.34820(16) 0.43834(14) 0.0310(4) Uani 1 1 d . . .
N2 N 0.41069(15) 0.78222(14) 0.28136(13) 0.0219(4) Uani 1 1 d . . .
H1N2 H 0.3836 0.7886 0.3491 0.026 Uiso 1 1 calc R . .
N3 N 0.66855(15) 0.90584(14) 0.36001(13) 0.0191(4) Uani 1 1 d . . .
N4 N 0.61050(16) 0.76425(15) 0.14123(14) 0.0240(4) Uani 1 1 d . . .
O1 O 0.76318(12) 0.69100(12) 0.27531(11) 0.0237(3) Uani 1 1 d . . .
O1S O 0.78650(16) 0.24330(14) 0.56412(13) 0.0394(4) Uani 1 1 d . . .
O2 O 0.57604(12) 0.70537(12) 0.41919(11) 0.0226(3) Uani 1 1 d . . .
S1 S 0.71102(5) 0.79606(5) -0.04869(4) 0.03236(15) Uani 1 1 d . . .
Fe1 Fe 0.59302(3) 0.73688(2) 0.28363(2) 0.01959(11) 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 O1 1.305(2) . ?
C1 C10 1.412(3) . ?
C1 C2 1.432(3) . ?
C1S N1S 1.453(3) . ?
C1S H1S1 0.9600 . ?
C1S H1S2 0.9600 . ?
C1S H1S3 0.9600 . ?
C2 C3 1.348(3) . ?
C2 H2 0.9300 . ?
C2S N1S 1.451(3) . ?
C2S H2S1 0.9600 . ?
C2S H2S2 0.9600 . ?
C2S H2S3 0.9600 . ?
C3 C4 1.418(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(3) . ?
C4 C9 1.420(3) . ?
C3S O1S 1.228(2) . ?
C3S N1S 1.332(3) . ?
C3S H3SA 0.9300 . ?
C5 C6 1.358(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.413(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.453(3) . ?
C10 C11 1.432(3) . ?
C11 N1 1.287(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.469(2) . ?
C12 C13 1.508(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.483(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.481(2) . ?
C14 C15 1.516(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.520(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N3 1.472(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N3 1.290(2) . ?
C17 C18 1.434(3) . ?
C17 H17 0.9300 . ?
C18 C27 1.405(3) . ?
C18 C19 1.440(3) . ?
C19 C24 1.414(3) . ?
C19 C20 1.420(3) . ?
C20 C21 1.373(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.396(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.363(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.407(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.424(3) . ?
C25 C26 1.351(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.420(3) . ?
C26 H26 0.9300 . ?
C27 O2 1.321(2) . ?
C28 N4 1.138(3) . ?
C28 S1 1.644(2) . ?
N1 Fe1 1.9070(16) . ?
N2 Fe1 2.0087(16) . ?
N2 H1N2 0.9100 . ?
N3 Fe1 1.9434(15) . ?
N4 Fe1 1.9447(17) . ?
O1 Fe1 1.8895(13) . ?
O2 Fe1 1.8780(13) . ?

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 C1 C10 125.38(17) . . ?
O1 C1 C2 116.09(17) . . ?
C10 C1 C2 118.53(18) . . ?
N1S C1S H1S1 109.5 . . ?
N1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
N1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C3 C2 C1 121.47(19) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N1S C2S H2S1 109.5 . . ?
N1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
N1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C2 C3 C4 121.95(19) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 121.85(19) . . ?
C5 C4 C9 119.3(2) . . ?
C3 C4 C9 118.78(19) . . ?
O1S C3S N1S 125.0(2) . . ?
O1S C3S H3SA 117.5 . . ?
N1S C3S H3SA 117.5 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.7(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 117.65(19) . . ?
C8 C9 C10 123.25(18) . . ?
C4 C9 C10 119.07(18) . . ?
C1 C10 C11 121.56(18) . . ?
C1 C10 C9 119.64(17) . . ?
C11 C10 C9 118.76(17) . . ?
N1 C11 C10 124.87(18) . . ?
N1 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
N1 C12 C13 106.23(15) . . ?
N1 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
N1 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
N2 C13 C12 107.58(16) . . ?
N2 C13 H13A 110.2 . . ?
C12 C13 H13A 110.2 . . ?
N2 C13 H13B 110.2 . . ?
C12 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
N2 C14 C15 114.13(16) . . ?
N2 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
N2 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 114.42(17) . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15B 108.7 . . ?
C16 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
N3 C16 C15 109.32(15) . . ?
N3 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N3 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N3 C17 C18 125.01(17) . . ?
N3 C17 H17 117.5 . . ?
C18 C17 H17 117.5 . . ?
C27 C18 C17 119.04(17) . . ?
C27 C18 C19 119.90(17) . . ?
C17 C18 C19 119.96(16) . . ?
C24 C19 C20 117.30(17) . . ?
C24 C19 C18 119.56(17) . . ?
C20 C19 C18 123.14(17) . . ?
C21 C20 C19 121.23(18) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 120.57(19) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.70(19) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 121.14(19) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C19 120.03(18) . . ?
C23 C24 C25 121.55(18) . . ?
C19 C24 C25 118.41(18) . . ?
C26 C25 C24 121.90(18) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C27 121.17(18) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
O2 C27 C18 123.82(17) . . ?
O2 C27 C26 117.07(17) . . ?
C18 C27 C26 119.01(17) . . ?
N4 C28 S1 178.29(19) . . ?
C11 N1 C12 120.26(16) . . ?
C11 N1 Fe1 126.82(13) . . ?
C12 N1 Fe1 112.91(12) . . ?
C3S N1S C2S 122.22(18) . . ?
C3S N1S C1S 121.39(19) . . ?
C2S N1S C1S 116.29(18) . . ?
C14 N2 C13 110.75(15) . . ?
C14 N2 Fe1 118.00(12) . . ?
C13 N2 Fe1 107.37(12) . . ?
C14 N2 H1N2 106.7 . . ?
C13 N2 H1N2 106.7 . . ?
Fe1 N2 H1N2 106.7 . . ?
C17 N3 C16 117.38(16) . . ?
C17 N3 Fe1 123.30(13) . . ?
C16 N3 Fe1 118.74(12) . . ?
C28 N4 Fe1 162.65(16) . . ?
C1 O1 Fe1 125.04(12) . . ?
C27 O2 Fe1 122.23(11) . . ?
O2 Fe1 O1 92.22(6) . . ?
O2 Fe1 N1 86.84(6) . . ?
O1 Fe1 N1 93.48(6) . . ?
O2 Fe1 N3 89.15(6) . . ?
O1 Fe1 N3 90.66(6) . . ?
N1 Fe1 N3 174.34(6) . . ?
O2 Fe1 N4 178.28(6) . . ?
O1 Fe1 N4 87.11(6) . . ?
N1 Fe1 N4 91.62(7) . . ?
N3 Fe1 N4 92.44(7) . . ?
O2 Fe1 N2 91.23(6) . . ?
O1 Fe1 N2 176.12(6) . . ?
N1 Fe1 N2 84.92(6) . . ?
N3 Fe1 N2 91.18(6) . . ?
N4 Fe1 N2 89.40(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1N2 O1S 0.91 2.16 2.941(2) 143.5 2_666

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.058
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d'_150K
_database_code_depnum_ccdc_archive 'CCDC 1030135'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H32 Fe N5 O3 Se'
_chemical_formula_weight         657.43

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2722(7)
_cell_length_b                   11.4128(6)
_cell_length_c                   12.8071(9)
_cell_angle_alpha                105.151(5)
_cell_angle_beta                 93.370(5)
_cell_angle_gamma                96.060(5)
_cell_volume                     1435.30(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5335
_cell_measurement_theta_min      2.9312
_cell_measurement_theta_max      33.3588

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             674
_exptl_absorpt_coefficient_mu    1.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9277
_exptl_absorpt_correction_T_max  1.0000
_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       
;
Rotation method data acquisition using omega and phi scans
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8956
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0658
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5026
_reflns_number_gt                3420
_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)+(0.1156P)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         5026
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1523
_refine_ls_goodness_of_fit_ref   0.909
_refine_ls_restrained_S_all      0.909
_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
C1 C 0.7950(5) 0.5917(5) 0.2117(4) 0.0244(11) Uani 1 1 d . . .
C1S C 0.8994(6) 0.4128(6) 0.3797(5) 0.0393(14) Uani 1 1 d . A .
H1S1 H 0.8848 0.4987 0.3924 0.059 Uiso 1 1 calc R . .
H1S2 H 0.8857 0.3722 0.3017 0.059 Uiso 1 1 calc R . .
H1S3 H 0.9896 0.4084 0.4065 0.059 Uiso 1 1 calc R . .
C2S C 0.6685(5) 0.3493(5) 0.4062(5) 0.0339(13) Uani 1 1 d . A .
H2S1 H 0.6167 0.3239 0.4602 0.051 Uiso 1 1 calc R . .
H2S2 H 0.6443 0.2911 0.3348 0.051 Uiso 1 1 calc R . .
H2S3 H 0.6507 0.4311 0.4030 0.051 Uiso 1 1 calc R . .
C4 C 0.8877(5) 0.3796(5) 0.0826(4) 0.0244(11) Uani 1 1 d . . .
C3SA C 0.8491(6) 0.2968(5) 0.5098(4) 0.0294(12) Uani 1 1 d . A 1
H3SA H 0.9414 0.3014 0.5256 0.035 Uiso 1 1 calc R A 1
C5 C 0.9327(5) 0.2721(5) 0.0188(4) 0.0305(13) Uani 1 1 d . . .
H5 H 1.0198 0.2766 -0.0023 0.037 Uiso 1 1 calc R . .
C6 C 0.8541(6) 0.1633(5) -0.0127(4) 0.0327(13) Uani 1 1 d . . .
H6 H 0.8864 0.0928 -0.0551 0.039 Uiso 1 1 calc R . .
C7 C 0.7263(6) 0.1552(5) 0.0172(4) 0.0308(13) Uani 1 1 d . . .
H7 H 0.6729 0.0782 -0.0023 0.037 Uiso 1 1 calc R . .
C8 C 0.6759(5) 0.2579(5) 0.0749(4) 0.0275(12) Uani 1 1 d . . .
H8 H 0.5878 0.2509 0.0937 0.033 Uiso 1 1 calc R . .
C9 C 0.7537(5) 0.3730(5) 0.1064(4) 0.0239(11) Uani 1 1 d . . .
C10 C 0.7066(5) 0.4848(4) 0.1667(4) 0.0224(11) Uani 1 1 d . . .
C11 C 0.5679(5) 0.4824(5) 0.1773(4) 0.0235(11) Uani 1 1 d . . .
H11 H 0.5141 0.4061 0.1505 0.028 Uiso 1 1 calc R . .
C12 C 0.3681(5) 0.5650(5) 0.2261(4) 0.0258(11) Uani 1 1 d . . .
H12A H 0.3458 0.5547 0.2976 0.031 Uiso 1 1 calc R . .
H12B H 0.3251 0.4930 0.1687 0.031 Uiso 1 1 calc R . .
C13 C 0.3234(5) 0.6819(5) 0.2093(4) 0.0258(11) Uani 1 1 d . . .
H13A H 0.3299 0.6842 0.1330 0.031 Uiso 1 1 calc R . .
H13B H 0.2309 0.6868 0.2260 0.031 Uiso 1 1 calc R . .
C14 C 0.3905(5) 0.9037(5) 0.2588(4) 0.0268(12) Uani 1 1 d . . .
H14A H 0.2980 0.9180 0.2684 0.032 Uiso 1 1 calc R . .
H14B H 0.4047 0.8958 0.1816 0.032 Uiso 1 1 calc R . .
C15 C 0.4800(5) 1.0136(5) 0.3287(4) 0.0269(12) Uani 1 1 d . . .
H15A H 0.4639 1.0225 0.4057 0.032 Uiso 1 1 calc R . .
H15B H 0.4561 1.0878 0.3098 0.032 Uiso 1 1 calc R . .
C16 C 0.6266(5) 1.0077(4) 0.3176(4) 0.0235(11) Uani 1 1 d . . .
H16A H 0.6440 0.9933 0.2404 0.028 Uiso 1 1 calc R . .
H16B H 0.6776 1.0864 0.3591 0.028 Uiso 1 1 calc R . .
C17 C 0.7367(5) 0.9377(4) 0.4514(4) 0.0208(11) Uani 1 1 d . . .
H17 H 0.7737 1.0208 0.4793 0.025 Uiso 1 1 calc R . .
C18 C 0.7628(5) 0.8546(5) 0.5154(4) 0.0230(11) Uani 1 1 d . . .
C19 C 0.8577(5) 0.8931(5) 0.6069(4) 0.0235(11) Uani 1 1 d . . .
C20 C 0.9470(5) 1.0046(4) 0.6323(4) 0.0228(11) Uani 1 1 d . . .
H20 H 0.9439 1.0564 0.5852 0.027 Uiso 1 1 calc R . .
C21 C 1.0358(5) 1.0387(5) 0.7212(4) 0.0250(11) Uani 1 1 d . . .
H21 H 1.0905 1.1148 0.7364 0.030 Uiso 1 1 calc R . .
C22 C 1.0475(5) 0.9626(5) 0.7908(4) 0.0273(12) Uani 1 1 d . . .
H22 H 1.1113 0.9856 0.8517 0.033 Uiso 1 1 calc R . .
C23 C 0.9654(5) 0.8545(5) 0.7695(4) 0.0280(12) Uani 1 1 d . . .
H23 H 0.9727 0.8034 0.8168 0.034 Uiso 1 1 calc R . .
C24 C 0.8709(5) 0.8176(4) 0.6797(4) 0.0243(11) Uani 1 1 d . . .
C25 C 0.7820(5) 0.7089(5) 0.6599(4) 0.0267(12) Uani 1 1 d . . .
H25 H 0.7880 0.6587 0.7081 0.032 Uiso 1 1 calc R . .
C26 C 0.6885(5) 0.6737(5) 0.5745(4) 0.0254(11) Uani 1 1 d . . .
H26 H 0.6295 0.6011 0.5653 0.030 Uiso 1 1 calc R . .
C27 C 0.6776(5) 0.7449(5) 0.4981(4) 0.0224(11) Uani 1 1 d . . .
C28 C 0.6464(5) 0.7806(4) 0.0622(4) 0.0247(11) Uani 1 1 d . . .
N1 N 0.5112(4) 0.5776(4) 0.2209(3) 0.0223(9) Uani 1 1 d . . .
N1S N 0.8075(4) 0.3521(4) 0.4368(4) 0.0299(10) Uani 1 1 d . . .
N2 N 0.4116(4) 0.7858(4) 0.2844(3) 0.0237(9) Uani 1 1 d . . .
H1N2 H 0.3859 0.7920 0.3539 0.028 Uiso 1 1 calc R . .
N3 N 0.6673(4) 0.9078(4) 0.3595(3) 0.0210(9) Uani 1 1 d . . .
N4 N 0.6084(4) 0.7699(4) 0.1426(3) 0.0238(9) Uani 1 1 d . . .
O1 O 0.7658(3) 0.6943(3) 0.2744(3) 0.0229(8) Uani 1 1 d . . .
O1S O 0.7769(4) 0.2400(3) 0.5585(3) 0.0351(9) Uani 1 1 d . . .
O2 O 0.5827(3) 0.7060(3) 0.4193(3) 0.0243(8) Uani 1 1 d . . .
Se1 Se 0.70467(5) 0.80049(5) -0.06225(4) 0.0296(2) Uani 1 1 d . . .
Fe1 Fe 0.59469(7) 0.74036(6) 0.28438(5) 0.0207(2) Uani 1 1 d . . .
C2 C 0.9296(5) 0.5897(5) 0.1894(4) 0.0256(11) Uani 1 1 d . . .
H2 H 0.9908 0.6604 0.2208 0.031 Uiso 1 1 calc R . .
C3 C 0.9718(5) 0.4902(5) 0.1252(4) 0.0265(12) Uani 1 1 d . . .
H3 H 1.0605 0.4946 0.1080 0.032 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.310(6) . ?
C1 C10 1.408(7) . ?
C1 C2 1.429(7) . ?
C1S N1S 1.453(7) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
C2S N1S 1.453(7) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
C4 C3 1.412(7) . ?
C4 C5 1.423(7) . ?
C4 C9 1.426(7) . ?
C3SA O1S 1.234(6) . ?
C3SA N1S 1.332(7) . ?
C3SA H3SA 0.9500 . ?
C5 C6 1.358(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.454(7) . ?
C10 C11 1.437(7) . ?
C11 N1 1.298(6) . ?
C11 H11 0.9500 . ?
C12 N1 1.469(6) . ?
C12 C13 1.519(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.492(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.499(6) . ?
C14 C15 1.515(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.528(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.469(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.285(6) . ?
C17 C18 1.440(7) . ?
C17 H17 0.9500 . ?
C18 C27 1.409(7) . ?
C18 C19 1.423(7) . ?
C19 C24 1.436(7) . ?
C19 C20 1.438(7) . ?
C20 C21 1.360(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.407(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.372(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.403(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.417(7) . ?
C25 C26 1.359(7) . ?
C25 H25 0.9500 . ?
C26 C27 1.432(7) . ?
C26 H26 0.9500 . ?
C27 O2 1.313(6) . ?
C28 N4 1.152(7) . ?
C28 Se1 1.796(6) . ?
N1 Fe1 1.908(4) . ?
N2 Fe1 2.003(4) . ?
N2 H1N2 0.9300 . ?
N3 Fe1 1.946(4) . ?
N4 Fe1 1.942(4) . ?
O1 Fe1 1.889(3) . ?
O2 Fe1 1.878(3) . ?
C2 C3 1.345(7) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?

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 C1 C10 125.9(4) . . ?
O1 C1 C2 116.0(4) . . ?
C10 C1 C2 118.1(4) . . ?
N1S C1S H1S1 109.5 . . ?
N1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
N1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
N1S C2S H2S1 109.5 . . ?
N1S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
N1S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C3 C4 C5 122.3(5) . . ?
C3 C4 C9 119.4(4) . . ?
C5 C4 C9 118.3(5) . . ?
O1S C3SA N1S 124.9(5) . . ?
O1S C3SA H3SA 117.5 . . ?
N1S C3SA H3SA 117.5 . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C7 120.0(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.7(5) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.8(5) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C4 118.4(5) . . ?
C8 C9 C10 123.6(5) . . ?
C4 C9 C10 117.9(5) . . ?
C1 C10 C11 121.6(4) . . ?
C1 C10 C9 120.5(4) . . ?
C11 C10 C9 117.9(4) . . ?
N1 C11 C10 124.4(5) . . ?
N1 C11 H11 117.8 . . ?
C10 C11 H11 117.8 . . ?
N1 C12 C13 106.1(4) . . ?
N1 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
N1 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
N2 C13 C12 106.9(4) . . ?
N2 C13 H13A 110.3 . . ?
C12 C13 H13A 110.3 . . ?
N2 C13 H13B 110.3 . . ?
C12 C13 H13B 110.3 . . ?
H13A C13 H13B 108.6 . . ?
N2 C14 C15 113.8(4) . . ?
N2 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
N2 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C16 114.8(4) . . ?
C14 C15 H15A 108.6 . . ?
C16 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
C16 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
N3 C16 C15 109.2(4) . . ?
N3 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
N3 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
N3 C17 C18 124.9(5) . . ?
N3 C17 H17 117.5 . . ?
C18 C17 H17 117.5 . . ?
C27 C18 C19 120.3(5) . . ?
C27 C18 C17 118.8(5) . . ?
C19 C18 C17 119.9(5) . . ?
C18 C19 C24 120.1(5) . . ?
C18 C19 C20 124.3(5) . . ?
C24 C19 C20 115.6(5) . . ?
C21 C20 C19 122.5(5) . . ?
C21 C20 H20 118.7 . . ?
C19 C20 H20 118.7 . . ?
C20 C21 C22 120.7(5) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 119.0(5) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 121.8(5) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C23 C24 C25 122.1(5) . . ?
C23 C24 C19 120.3(5) . . ?
C25 C24 C19 117.5(5) . . ?
C26 C25 C24 122.5(5) . . ?
C26 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C25 C26 C27 120.8(5) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
O2 C27 C18 124.3(5) . . ?
O2 C27 C26 116.9(5) . . ?
C18 C27 C26 118.7(5) . . ?
N4 C28 Se1 178.8(4) . . ?
C11 N1 C12 119.9(4) . . ?
C11 N1 Fe1 126.9(4) . . ?
C12 N1 Fe1 113.3(3) . . ?
C3SA N1S C2S 121.8(5) . . ?
C3SA N1S C1S 121.4(5) . . ?
C2S N1S C1S 116.8(5) . . ?
C13 N2 C14 110.3(4) . . ?
C13 N2 Fe1 108.1(3) . . ?
C14 N2 Fe1 117.6(3) . . ?
C13 N2 H1N2 106.8 . . ?
C14 N2 H1N2 106.8 . . ?
Fe1 N2 H1N2 106.8 . . ?
C17 N3 C16 117.2(4) . . ?
C17 N3 Fe1 123.5(3) . . ?
C16 N3 Fe1 118.7(3) . . ?
C28 N4 Fe1 163.6(4) . . ?
C1 O1 Fe1 124.9(3) . . ?
C27 O2 Fe1 122.0(3) . . ?
O2 Fe1 O1 91.94(15) . . ?
O2 Fe1 N1 86.71(16) . . ?
O1 Fe1 N1 93.58(15) . . ?
O2 Fe1 N4 177.93(15) . . ?
O1 Fe1 N4 86.90(16) . . ?
N1 Fe1 N4 91.65(18) . . ?
O2 Fe1 N3 89.30(16) . . ?
O1 Fe1 N3 90.45(15) . . ?
N1 Fe1 N3 174.42(17) . . ?
N4 Fe1 N3 92.42(17) . . ?
O2 Fe1 N2 91.32(16) . . ?
O1 Fe1 N2 176.26(16) . . ?
N1 Fe1 N2 84.79(16) . . ?
N4 Fe1 N2 89.78(17) . . ?
N3 Fe1 N2 91.41(16) . . ?
C3 C2 C1 121.7(5) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 121.8(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         2.152
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.169
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1e
_database_code_depnum_ccdc_archive 'CCDC 1030136'
_audit_update_record             
;
2014-10-20 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H31 Fe N4 O3 S2'
_chemical_formula_weight         615.56

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   10.2094(3)
_cell_length_b                   11.0128(4)
_cell_length_c                   12.9469(4)
_cell_angle_alpha                98.641(3)
_cell_angle_beta                 92.784(2)
_cell_angle_gamma                95.509(3)
_cell_volume                     1429.56(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    8881
_cell_measurement_theta_min      3.0803
_cell_measurement_theta_max      33.3393

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             642
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96622
_exptl_absorpt_correction_T_max  1.00000
_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      160(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       
;
Rotation method data acquisition using omega and phi scans
;
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13601
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5009
_reflns_number_gt                4001
_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)+(0.0793P)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         5009
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2024(2) 0.4391(2) 0.7910(2) 0.0270(6) Uani 1 1 d . . .
C2 C 0.0701(3) 0.4445(3) 0.8187(2) 0.0357(7) Uani 1 1 d . . .
H2 H 0.0059 0.3772 0.7928 0.043 Uiso 1 1 calc R . .
C3 C 0.0332(3) 0.5440(3) 0.8814(2) 0.0363(7) Uani 1 1 d . . .
H3 H -0.0550 0.5427 0.9019 0.044 Uiso 1 1 calc R . .
C4 C 0.1229(3) 0.6491(3) 0.9168(2) 0.0293(6) Uani 1 1 d . . .
C5 C 0.0820(3) 0.7554(3) 0.9773(2) 0.0369(7) Uani 1 1 d . . .
H5 H -0.0049 0.7532 1.0006 0.044 Uiso 1 1 calc R . .
C6 C 0.1659(3) 0.8607(3) 1.0025(2) 0.0375(7) Uani 1 1 d . . .
H6 H 0.1378 0.9315 1.0432 0.045 Uiso 1 1 calc R . .
C7 C 0.2924(3) 0.8641(3) 0.9684(2) 0.0341(7) Uani 1 1 d . . .
H7 H 0.3490 0.9391 0.9830 0.041 Uiso 1 1 calc R . .
C8 C 0.3376(3) 0.7617(2) 0.9142(2) 0.0284(6) Uani 1 1 d . . .
H8 H 0.4258 0.7661 0.8936 0.034 Uiso 1 1 calc R . .
C9 C 0.2551(3) 0.6497(2) 0.88823(19) 0.0259(6) Uani 1 1 d . . .
C10 C 0.2976(2) 0.5380(2) 0.8306(2) 0.0244(6) Uani 1 1 d . . .
C11 C 0.4355(3) 0.5313(2) 0.81842(19) 0.0245(6) Uani 1 1 d . . .
H11 H 0.4937 0.6023 0.8468 0.029 Uiso 1 1 calc R . .
C12 C 0.6320(2) 0.4426(2) 0.7710(2) 0.0291(6) Uani 1 1 d . . .
H12A H 0.6739 0.5126 0.8229 0.035 Uiso 1 1 calc R . .
H12B H 0.6605 0.4543 0.7009 0.035 Uiso 1 1 calc R . .
C13 C 0.6715(2) 0.3215(2) 0.7984(2) 0.0291(6) Uani 1 1 d . . .
H13A H 0.7667 0.3169 0.7895 0.035 Uiso 1 1 calc R . .
H13B H 0.6550 0.3161 0.8724 0.035 Uiso 1 1 calc R . .
C14 C 0.6137(3) 0.0987(3) 0.7626(2) 0.0315(6) Uani 1 1 d . . .
H14A H 0.5894 0.1023 0.8360 0.038 Uiso 1 1 calc R . .
H14B H 0.7087 0.0876 0.7612 0.038 Uiso 1 1 calc R . .
C15 C 0.5361(3) -0.0125(3) 0.6971(2) 0.0329(7) Uani 1 1 d . . .
H15A H 0.5646 -0.0880 0.7205 0.040 Uiso 1 1 calc R . .
H15B H 0.5585 -0.0144 0.6233 0.040 Uiso 1 1 calc R . .
C16 C 0.3869(3) -0.0165(2) 0.7013(2) 0.0291(6) Uani 1 1 d . . .
H16A H 0.3448 -0.0981 0.6664 0.035 Uiso 1 1 calc R . .
H16B H 0.3633 -0.0050 0.7752 0.035 Uiso 1 1 calc R . .
C17 C 0.2749(2) 0.0471(2) 0.5591(2) 0.0242(6) Uani 1 1 d . . .
H17 H 0.2481 -0.0386 0.5390 0.029 Uiso 1 1 calc R . .
C18 C 0.2409(2) 0.1272(2) 0.48719(19) 0.0216(5) Uani 1 1 d . . .
C19 C 0.1500(2) 0.0805(2) 0.3984(2) 0.0248(6) Uani 1 1 d . . .
C20 C 0.0741(3) -0.0355(2) 0.3874(2) 0.0291(6) Uani 1 1 d . . .
H20 H 0.0829 -0.0862 0.4401 0.035 Uiso 1 1 calc R . .
C21 C -0.0127(3) -0.0760(3) 0.3013(2) 0.0348(7) Uani 1 1 d . . .
H21 H -0.0611 -0.1552 0.2944 0.042 Uiso 1 1 calc R . .
C22 C -0.0300(3) -0.0024(3) 0.2248(2) 0.0380(7) Uani 1 1 d . . .
H22 H -0.0919 -0.0304 0.1669 0.046 Uiso 1 1 calc R . .
C23 C 0.0409(3) 0.1088(3) 0.2323(2) 0.0362(7) Uani 1 1 d . . .
H23 H 0.0295 0.1582 0.1790 0.043 Uiso 1 1 calc R . .
C24 C 0.1316(3) 0.1523(3) 0.3184(2) 0.0287(6) Uani 1 1 d . . .
C25 C 0.2072(3) 0.2690(3) 0.3266(2) 0.0318(6) Uani 1 1 d . . .
H25 H 0.1961 0.3182 0.2731 0.038 Uiso 1 1 calc R . .
C26 C 0.2948(3) 0.3116(2) 0.4089(2) 0.0294(6) Uani 1 1 d . . .
H26 H 0.3455 0.3890 0.4108 0.035 Uiso 1 1 calc R . .
C27 C 0.3131(2) 0.2438(2) 0.49264(19) 0.0246(6) Uani 1 1 d . . .
C28 C 0.3362(2) 0.2181(2) 0.9474(2) 0.0258(6) Uani 1 1 d . . .
N1 N 0.48760(19) 0.43714(19) 0.77214(16) 0.0223(5) Uani 1 1 d . . .
N2 N 0.5929(2) 0.21738(19) 0.72839(16) 0.0254(5) Uani 1 1 d . . .
H1N2 H 0.6256 0.2151 0.6624 0.030 Uiso 1 1 calc R . .
N3 N 0.3387(2) 0.08072(18) 0.64908(16) 0.0228(5) Uani 1 1 d . . .
N4 N 0.3715(2) 0.2218(2) 0.86467(18) 0.0315(5) Uani 1 1 d . . .
O1 O 0.22921(17) 0.34088(16) 0.72821(15) 0.0328(5) Uani 1 1 d . . .
O2 O 0.40049(17) 0.29098(16) 0.56916(13) 0.0275(4) Uani 1 1 d . . .
S1 S 0.28776(7) 0.21016(7) 1.06426(6) 0.0376(2) Uani 1 1 d . . .
Fe1 Fe 0.39012(3) 0.26378(3) 0.71456(3) 0.02201(14) Uani 1 1 d . . .
C29 C 0.3419(4) 0.6048(3) 0.5747(3) 0.0639(10) Uani 1 1 d . . .
H29A H 0.4215 0.5948 0.5361 0.096 Uiso 1 1 calc R . .
H29B H 0.3184 0.5303 0.6056 0.096 Uiso 1 1 calc R . .
H29C H 0.3587 0.6762 0.6304 0.096 Uiso 1 1 calc R . .
C30 C 0.0916(5) 0.6505(5) 0.5824(5) 0.1088(19) Uani 1 1 d . . .
H30A H 0.1183 0.7271 0.6309 0.163 Uiso 1 1 calc R . .
H30B H 0.0847 0.5807 0.6213 0.163 Uiso 1 1 calc R . .
H30C H 0.0058 0.6563 0.5470 0.163 Uiso 1 1 calc R . .
O3 O 0.2478(2) 0.7504(2) 0.45648(18) 0.0520(6) Uani 1 1 d . . .
S2 S 0.21065(9) 0.62809(7) 0.48805(7) 0.0475(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
C1 O1 1.311(3) . ?
C1 C10 1.406(4) . ?
C1 C2 1.419(4) . ?
C2 C3 1.358(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(4) . ?
C4 C9 1.417(4) . ?
C5 C6 1.361(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.367(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.455(4) . ?
C10 C11 1.432(4) . ?
C11 N1 1.291(3) . ?
C11 H11 0.9500 . ?
C12 N1 1.470(3) . ?
C12 C13 1.516(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 N2 1.490(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N2 1.472(3) . ?
C14 C15 1.512(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.524(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N3 1.460(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 N3 1.292(3) . ?
C17 C18 1.428(4) . ?
C17 H17 0.9500 . ?
C18 C27 1.408(3) . ?
C18 C19 1.440(4) . ?
C19 C24 1.409(4) . ?
C19 C20 1.413(4) . ?
C20 C21 1.381(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.349(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.409(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.422(4) . ?
C25 C26 1.354(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.420(4) . ?
C26 H26 0.9500 . ?
C27 O2 1.311(3) . ?
C28 N4 1.152(3) . ?
C28 S1 1.626(3) . ?
N1 Fe1 2.080(2) . ?
N2 Fe1 2.185(2) . ?
N2 H1N2 0.9300 . ?
N3 Fe1 2.073(2) . ?
N4 Fe1 2.077(2) . ?
O1 Fe1 1.9240(18) . ?
O2 Fe1 1.9564(17) . ?
C29 S2 1.768(4) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 S2 1.772(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O3 S2 1.485(2) . ?

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 C1 C10 123.2(2) . . ?
O1 C1 C2 117.6(2) . . ?
C10 C1 C2 119.3(2) . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 C9 119.2(2) . . ?
C5 C4 C9 119.6(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C8 C7 C6 121.4(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.9(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C4 117.5(2) . . ?
C8 C9 C10 123.4(2) . . ?
C4 C9 C10 119.1(2) . . ?
C1 C10 C11 122.2(2) . . ?
C1 C10 C9 119.0(2) . . ?
C11 C10 C9 118.9(2) . . ?
N1 C11 C10 125.6(2) . . ?
N1 C11 H11 117.2 . . ?
C10 C11 H11 117.2 . . ?
N1 C12 C13 107.3(2) . . ?
N1 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
N1 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
N2 C13 C12 109.0(2) . . ?
N2 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N2 C14 C15 114.5(2) . . ?
N2 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N2 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C16 115.1(2) . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
N3 C16 C15 109.9(2) . . ?
N3 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
N3 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N3 C17 C18 125.8(2) . . ?
N3 C17 H17 117.1 . . ?
C18 C17 H17 117.1 . . ?
C27 C18 C17 119.7(2) . . ?
C27 C18 C19 119.6(2) . . ?
C17 C18 C19 119.7(2) . . ?
C24 C19 C20 117.0(2) . . ?
C24 C19 C18 120.1(2) . . ?
C20 C19 C18 122.9(2) . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 120.7(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C19 C24 C23 120.7(3) . . ?
C19 C24 C25 118.4(2) . . ?
C23 C24 C25 120.9(3) . . ?
C26 C25 C24 121.4(3) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 121.8(2) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 H26 119.1 . . ?
O2 C27 C18 123.3(2) . . ?
O2 C27 C26 118.1(2) . . ?
C18 C27 C26 118.5(2) . . ?
N4 C28 S1 178.8(3) . . ?
C11 N1 C12 119.0(2) . . ?
C11 N1 Fe1 126.51(17) . . ?
C12 N1 Fe1 113.93(15) . . ?
C14 N2 C13 110.7(2) . . ?
C14 N2 Fe1 117.37(16) . . ?
C13 N2 Fe1 107.68(15) . . ?
C14 N2 H1N2 106.9 . . ?
C13 N2 H1N2 106.9 . . ?
Fe1 N2 H1N2 106.9 . . ?
C17 N3 C16 117.2(2) . . ?
C17 N3 Fe1 123.41(17) . . ?
C16 N3 Fe1 119.15(16) . . ?
C28 N4 Fe1 162.6(2) . . ?
C1 O1 Fe1 130.52(16) . . ?
C27 O2 Fe1 124.88(15) . . ?
O1 Fe1 O2 92.02(8) . . ?
O1 Fe1 N3 107.15(8) . . ?
O2 Fe1 N3 84.39(8) . . ?
O1 Fe1 N4 88.17(9) . . ?
O2 Fe1 N4 175.64(8) . . ?
N3 Fe1 N4 91.39(8) . . ?
O1 Fe1 N1 86.52(8) . . ?
O2 Fe1 N1 92.54(8) . . ?
N3 Fe1 N1 166.06(8) . . ?
N4 Fe1 N1 91.81(8) . . ?
O1 Fe1 N2 165.25(8) . . ?
O2 Fe1 N2 93.88(8) . . ?
N3 Fe1 N2 86.89(8) . . ?
N4 Fe1 N2 86.97(9) . . ?
N1 Fe1 N2 79.73(8) . . ?
S2 C29 H29A 109.5 . . ?
S2 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
S2 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
S2 C30 H30A 109.5 . . ?
S2 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
S2 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O3 S2 C29 105.37(16) . . ?
O3 S2 C30 106.73(19) . . ?
C29 S2 C30 97.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.073
