# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1060123'
_audit_update_record             
;
2015-04-16 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15.50 H12 Fe N8 O1.5 S2'
_chemical_formula_weight         454.30

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P43

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   8.5067(4)
_cell_length_b                   8.5067(4)
_cell_length_c                   26.288(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1902.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(1)
_cell_measurement_reflns_used    3520
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      29.01

_exptl_crystal_description       prismatic
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             924
_exptl_absorpt_coefficient_mu    1.040
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8596
_exptl_absorpt_correction_T_max  0.9402
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(1)
_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            5708
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0682
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         29.01
_reflns_number_total             3520
_reflns_number_gt                3062
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'HKL DENZO'
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1689P)²+16.9868P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_number_reflns         3520
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0645
_refine_ls_wR_factor_ref         0.1849
_refine_ls_wR_factor_gt          0.1685
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.041
_refine_ls_shift/su_mean         0.023

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
Fe Fe 0.09277(10) 0.91870(10) 0.93939(4) 0.0213(2) Uani 1 1 d . . .
S1 S 0.5896(3) 1.1200(5) 0.9833(3) 0.152(3) Uani 1 1 d . . .
S2 S 0.3104(8) 0.4264(5) 0.8962(4) 0.090(3) Uani 0.50 1 d P . .
S2A S 0.3406(4) 0.4241(4) 0.9399(2) 0.0403(9) Uani 0.50 1 d P . .
N1 N 0.1312(6) 0.9793(6) 0.8672(2) 0.0230(11) Uani 1 1 d . . .
N2 N -0.1180(6) 0.8564(6) 0.9119(2) 0.0224(11) Uani 1 1 d . . .
N3 N 0.0022(6) 1.1302(5) 0.9576(2) 0.0192(10) Uani 1 1 d . . .
N4 N 0.0452(6) 0.8710(6) 1.0115(2) 0.0242(11) Uani 1 1 d . . .
N5 N 0.3000(6) 0.9951(7) 0.9587(2) 0.0290(12) Uani 1 1 d . . .
N6 N 0.1753(7) 0.7090(7) 0.9281(2) 0.0300(13) Uani 1 1 d . . .
N7 N -0.3988(6) 0.7954(7) 0.8572(2) 0.0299(12) Uani 1 1 d . . .
N8 N -0.4060(6) 0.8776(7) 0.7513(2) 0.0277(12) Uani 1 1 d . . .
C1 C 0.2558(7) 1.0383(7) 0.8438(3) 0.0255(13) Uani 1 1 d . . .
H1 H 0.3459 1.0594 0.8626 0.031 Uiso 1 1 calc R . .
C2 C 0.0050(7) 0.9512(7) 0.8374(2) 0.0187(11) Uani 1 1 d . . .
C3 C -0.1334(6) 0.8872(6) 0.8616(2) 0.0183(11) Uani 1 1 d . . .
C4 C -0.2705(7) 0.8606(7) 0.8343(3) 0.0249(13) Uani 1 1 d . . .
C5 C -0.2751(7) 0.8996(7) 0.7797(3) 0.0215(12) Uani 1 1 d . . .
C6 C -0.3812(8) 0.7639(9) 0.9059(3) 0.0321(15) Uani 1 1 d . . .
H6 H -0.4663 0.7188 0.9226 0.039 Uiso 1 1 calc R . .
C7 C -0.2444(7) 0.7927(7) 0.9351(3) 0.0266(13) Uani 1 1 d . . .
H7 H -0.2417 0.7682 0.9695 0.032 Uiso 1 1 calc R . .
C8 C -0.3958(7) 0.9176(8) 0.7035(3) 0.0289(14) Uani 1 1 d . . .
H8 H -0.4839 0.9038 0.6831 0.035 Uiso 1 1 calc R . .
C9 C -0.0191(7) 1.2583(7) 0.9308(3) 0.0282(15) Uani 1 1 d . . .
H9 H 0.0076 1.2591 0.8965 0.034 Uiso 1 1 calc R . .
C10 C -0.0385(6) 1.1369(7) 1.0069(3) 0.0195(11) Uani 1 1 d . . .
C11 C -0.0145(7) 0.9978(7) 1.0358(3) 0.0205(12) Uani 1 1 d . . .
C12 C 0.0704(7) 0.7443(7) 1.0404(3) 0.0248(13) Uani 1 1 d . . .
H12 H 0.1099 0.6536 1.0253 0.030 Uiso 1 1 calc R . .
C13 C 0.4165(9) 1.0466(10) 0.9683(4) 0.051(2) Uani 1 1 d . . .
C14 C 0.2382(10) 0.5924(10) 0.9258(6) 0.072(4) Uani 1 1 d . . .
O1 O -0.7047(7) 0.6991(8) 0.8000(3) 0.0535(16) Uani 1 1 d . . .
C15 C -0.676(3) 0.535(2) 0.7911(9) 0.148(9) Uani 1 1 d . . .
C16 C -0.327(3) 1.290(2) 0.8381(11) 0.075(8) Uani 0.50 1 d P . .
O2 O -0.403(3) 1.274(7) 0.779(2) 0.31(3) Uani 0.50 1 d P . .


_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
Fe N1 1.993(6) . ?
Fe N2 2.005(5) . ?
Fe N3 2.015(5) . ?
Fe N4 1.980(6) . ?
Fe N5 1.946(5) . ?
Fe N6 1.940(6) . ?
S1 C13 1.647(8) . ?
S2 C14 1.725(11) . ?
S2A C14 1.716(10) . ?
N1 C1 1.324(8) . ?
N1 C2 1.351(8) . ?
N2 C7 1.350(8) . ?
N2 C3 1.352(8) . ?
N3 C9 1.311(8) . ?
N3 C10 1.344(8) . ?
N4 C12 1.336(8) . ?
N4 C11 1.353(8) . ?
N5 C13 1.112(10) . ?
N6 C14 1.129(11) . ?
N7 C6 1.316(10) . ?
N7 C4 1.365(8) . ?
N8 C8 1.306(10) . ?
N8 C5 1.353(8) . ?
C1 C12 1.431(10) 3_664 ?
C1 H1 0.9300 . ?
C2 C11 1.387(9) 3_664 ?
C2 C3 1.446(8) . ?
C3 C4 1.389(9) . ?
C4 C5 1.474(9) . ?
C5 C10 1.421(8) 3_664 ?
C6 C7 1.415(10) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.419(9) 3_664 ?
C8 H8 0.9300 . ?
C9 C8 1.419(9) 4_465 ?
C9 H9 0.9300 . ?
C10 C11 1.420(8) . ?
C10 C5 1.421(8) 4_465 ?
C11 C2 1.387(9) 4_465 ?
C12 C1 1.431(10) 4_465 ?
C12 H12 0.9300 . ?
O1 C15 1.44(2) . ?
C16 O2 1.68(6) . ?

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
N1 Fe N2 82.6(2) . . ?
N1 Fe N3 93.3(2) . . ?
N1 Fe N4 176.2(2) . . ?
N5 Fe N1 90.8(2) . . ?
N6 Fe N1 91.9(2) . . ?
N3 Fe N2 88.9(2) . . ?
N4 Fe N2 96.2(2) . . ?
N5 Fe N2 173.0(3) . . ?
N6 Fe N2 91.4(2) . . ?
N4 Fe N3 83.0(2) . . ?
N5 Fe N3 89.2(2) . . ?
N6 Fe N3 174.8(2) . . ?
N5 Fe N4 90.2(2) . . ?
N6 Fe N4 91.8(2) . . ?
N6 Fe N5 91.1(3) . . ?
C1 N1 C2 115.6(6) . . ?
C1 N1 Fe 132.2(5) . . ?
C2 N1 Fe 112.1(4) . . ?
C7 N2 C3 116.2(6) . . ?
C7 N2 Fe 130.9(5) . . ?
C3 N2 Fe 112.8(4) . . ?
C9 N3 C10 116.7(5) . . ?
C9 N3 Fe 131.9(5) . . ?
C10 N3 Fe 111.4(4) . . ?
C12 N4 C11 115.8(6) . . ?
C12 N4 Fe 132.6(5) . . ?
C11 N4 Fe 111.4(5) . . ?
C13 N5 Fe 175.9(7) . . ?
C14 N6 Fe 171.1(8) . . ?
C6 N7 C4 114.8(6) . . ?
C8 N8 C5 116.1(6) . . ?
N1 C1 C12 121.9(6) . 3_664 ?
N1 C1 H1 119.1 . . ?
C12 C1 H1 119.1 3_664 . ?
N1 C2 C11 123.0(5) . 3_664 ?
N1 C2 C3 117.2(6) . . ?
C11 C2 C3 119.8(5) 3_664 . ?
N2 C3 C4 123.7(5) . . ?
N2 C3 C2 115.2(5) . . ?
C4 C3 C2 121.1(6) . . ?
N7 C4 C3 120.7(6) . . ?
N7 C4 C5 120.0(6) . . ?
C3 C4 C5 119.4(5) . . ?
N8 C5 C10 120.0(6) . 3_664 ?
N8 C5 C4 121.9(6) . . ?
C10 C5 C4 118.1(6) 3_664 . ?
N7 C6 C7 125.9(6) . . ?
N7 C6 H6 117.1 . . ?
C7 C6 H6 117.1 . . ?
N2 C7 C6 118.6(7) . . ?
N2 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
N8 C8 C9 124.0(6) . 3_664 ?
N8 C8 H8 118.0 . . ?
C9 C8 H8 118.0 3_664 . ?
N3 C9 C8 120.7(7) . 4_465 ?
N3 C9 H9 119.6 . . ?
C8 C9 H9 119.6 4_465 . ?
N3 C10 C11 116.3(5) . . ?
N3 C10 C5 122.5(6) . 4_465 ?
C11 C10 C5 121.2(6) . 4_465 ?
N4 C11 C10 117.8(6) . . ?
N4 C11 C2 121.7(6) . 4_465 ?
C10 C11 C2 120.4(5) . 4_465 ?
N4 C12 C1 121.9(6) . 4_465 ?
N4 C12 H12 119.1 . . ?
C1 C12 H12 119.1 4_465 . ?
N5 C13 S1 178.8(11) . . ?
N6 C14 S2 155.8(14) . . ?
N6 C14 S2A 164.2(13) . . ?
S2 C14 S2A 39.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.871
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.171
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.109
