# 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_akh_EJMC_1
_database_code_depnum_ccdc_archive 'CCDC 1009326'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Fe N9 O3 S2'
_chemical_formula_sum            'C14 H14 Fe N9 O3 S2'
_chemical_formula_weight         476.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   8.5486(10)
_cell_length_b                   9.3634(11)
_cell_length_c                   12.5188(14)
_cell_angle_alpha                102.762(4)
_cell_angle_beta                 101.769(4)
_cell_angle_gamma                91.573(4)
_cell_volume                     953.99(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             486
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6224
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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  'Bruker Smart CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19873
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         30.13
_reflns_number_total             5488
_reflns_number_gt                4876
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2σ(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)+(0.0787P)²+0.0908P] 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     SHELXL
_refine_ls_extinction_coef       0.051(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5488
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S2 S 0.55471(5) 0.44542(6) 0.69180(4) 0.04036(13) Uani 1 1 d . . .
Fe2 Fe 0.80283(2) 0.54988(2) 0.735126(17) 0.02681(10) Uani 1 1 d . . .
S1 S 0.91732(6) 0.33864(5) 0.72901(4) 0.03971(13) Uani 1 1 d . . .
N2 N 0.81499(16) 0.51736(15) 0.58057(11) 0.0286(3) Uani 1 1 d . . .
N3 N 0.85097(19) 0.38761(16) 0.51892(12) 0.0356(3) Uani 1 1 d . . .
N4 N 0.9290(2) 0.16056(19) 0.53510(15) 0.0518(4) Uani 1 1 d . . .
H4N H 0.9219 0.1356 0.4638 0.062 Uiso 1 1 calc R . .
H5N H 0.9579 0.0989 0.5758 0.062 Uiso 1 1 calc R . .
O3 O 0.7772(4) 0.9008(2) 0.14494(17) 0.0959(8) Uani 1 1 d . . .
O1 O 0.9409(3) 1.0204(2) 0.29852(18) 0.0703(5) Uani 1 1 d . . .
O2 O 0.7410(3) 0.8810(3) 0.30494(18) 0.0802(6) Uani 1 1 d . . .
N1 N 0.72981(16) 0.74179(15) 0.70664(11) 0.0306(3) Uani 1 1 d . . .
C6 C 0.7783(2) 0.62417(19) 0.53142(14) 0.0337(3) Uani 1 1 d . . .
H6 H 0.7827 0.6180 0.4569 0.040 Uiso 1 1 calc R . .
C7 C 0.8951(2) 0.29456(19) 0.58246(14) 0.0359(3) Uani 1 1 d . . .
N5 N 1.01577(16) 0.65636(15) 0.81126(11) 0.0303(3) Uani 1 1 d . . .
N9 N 0.8198(3) 0.9350(2) 0.24774(18) 0.0585(5) Uani 1 1 d . . .
C14 C 0.5380(2) 0.4605(2) 0.83045(15) 0.0383(4) Uani 1 1 d . . .
N8 N 0.4075(2) 0.3979(2) 0.84838(15) 0.0562(5) Uani 1 1 d . . .
H9N H 0.3947 0.4059 0.9158 0.067 Uiso 1 1 calc R . .
H8N H 0.3357 0.3495 0.7926 0.067 Uiso 1 1 calc R . .
N7 N 0.64645(19) 0.53457(18) 0.91852(12) 0.0390(3) Uani 1 1 d . . .
N6 N 0.77910(17) 0.58292(16) 0.88747(11) 0.0313(3) Uani 1 1 d . . .
C5 C 0.73019(19) 0.75267(19) 0.60021(14) 0.0322(3) Uani 1 1 d . . .
C4 C 0.6836(2) 0.8780(2) 0.56272(17) 0.0433(4) Uani 1 1 d . . .
H4 H 0.6870 0.8852 0.4903 0.052 Uiso 1 1 calc R . .
C3 C 0.6323(3) 0.9914(2) 0.6360(2) 0.0492(5) Uani 1 1 d . . .
H3 H 0.6001 1.0759 0.6130 0.059 Uiso 1 1 calc R . .
C2 C 0.6292(2) 0.9784(2) 0.74313(19) 0.0474(5) Uani 1 1 d . . .
H2 H 0.5921 1.0526 0.7923 0.057 Uiso 1 1 calc R . .
C1 C 0.6820(2) 0.8535(2) 0.77659(16) 0.0388(4) Uani 1 1 d . . .
H1 H 0.6843 0.8470 0.8500 0.047 Uiso 1 1 calc R . .
C8 C 1.1378(2) 0.6844(2) 0.76493(16) 0.0381(4) Uani 1 1 d . . .
H8 H 1.1244 0.6588 0.6873 0.046 Uiso 1 1 calc R . .
C9 C 1.2829(2) 0.7502(3) 0.8297(2) 0.0496(5) Uani 1 1 d . . .
H9 H 1.3665 0.7674 0.7958 0.059 Uiso 1 1 calc R . .
C10 C 1.3035(3) 0.7903(3) 0.9442(2) 0.0579(6) Uani 1 1 d . . .
H10 H 1.4009 0.8349 0.9885 0.069 Uiso 1 1 calc R . .
C11 C 1.1779(3) 0.7637(3) 0.99309(18) 0.0523(5) Uani 1 1 d . . .
H11 H 1.1890 0.7909 1.0705 0.063 Uiso 1 1 calc R . .
C12 C 1.0347(2) 0.6955(2) 0.92452(14) 0.0358(4) Uani 1 1 d . . .
C13 C 0.8976(2) 0.6544(2) 0.96491(14) 0.0378(4) Uani 1 1 d . . .
H13 H 0.8942 0.6773 1.0405 0.045 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
S2 C14 1.7455(18) . ?
S2 Fe2 2.2209(5) . ?
Fe2 N2 1.9159(13) . ?
Fe2 N6 1.9170(14) . ?
Fe2 N5 1.9972(14) . ?
Fe2 N1 1.9999(14) . ?
Fe2 S1 2.2240(5) . ?
S1 C7 1.7582(18) . ?
N2 C6 1.299(2) . ?
N2 N3 1.3673(19) . ?
N3 C7 1.317(2) . ?
N4 C7 1.331(2) . ?
N4 H4N 0.8600 . ?
N4 H5N 0.8600 . ?
O3 N9 1.230(3) . ?
O1 N9 1.256(3) . ?
O2 N9 1.249(3) . ?
N1 C1 1.339(2) . ?
N1 C5 1.359(2) . ?
C6 C5 1.439(2) . ?
C6 H6 0.9300 . ?
N5 C8 1.339(2) . ?
N5 C12 1.358(2) . ?
C14 N8 1.328(2) . ?
C14 N7 1.329(2) . ?
N8 H9N 0.8600 . ?
N8 H8N 0.8600 . ?
N7 N6 1.3679(19) . ?
N6 C13 1.300(2) . ?
C5 C4 1.396(2) . ?
C4 C3 1.387(3) . ?
C4 H4 0.9300 . ?
C3 C2 1.378(3) . ?
C3 H3 0.9300 . ?
C2 C1 1.384(3) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.443(2) . ?
C13 H13 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
C14 S2 Fe2 95.25(6) . . ?
N2 Fe2 N6 177.08(6) . . ?
N2 Fe2 N5 101.42(6) . . ?
N6 Fe2 N5 81.09(6) . . ?
N2 Fe2 N1 81.40(6) . . ?
N6 Fe2 N1 97.30(6) . . ?
N5 Fe2 N1 87.18(6) . . ?
N2 Fe2 S2 92.27(4) . . ?
N6 Fe2 S2 85.18(4) . . ?
N5 Fe2 S2 166.18(4) . . ?
N1 Fe2 S2 93.06(4) . . ?
N2 Fe2 S1 84.57(4) . . ?
N6 Fe2 S1 97.02(5) . . ?
N5 Fe2 S1 88.97(4) . . ?
N1 Fe2 S1 164.41(4) . . ?
S2 Fe2 S1 94.26(2) . . ?
C7 S1 Fe2 94.79(6) . . ?
C6 N2 N3 119.00(13) . . ?
C6 N2 Fe2 116.83(11) . . ?
N3 N2 Fe2 124.08(11) . . ?
C7 N3 N2 111.32(13) . . ?
C7 N4 H4N 120.0 . . ?
C7 N4 H5N 120.0 . . ?
H4N N4 H5N 120.0 . . ?
C1 N1 C5 119.05(15) . . ?
C1 N1 Fe2 128.79(12) . . ?
C5 N1 Fe2 112.16(11) . . ?
N2 C6 C5 115.36(14) . . ?
N2 C6 H6 122.3 . . ?
C5 C6 H6 122.3 . . ?
N3 C7 N4 119.21(16) . . ?
N3 C7 S1 123.55(13) . . ?
N4 C7 S1 117.21(14) . . ?
C8 N5 C12 119.18(15) . . ?
C8 N5 Fe2 128.13(12) . . ?
C12 N5 Fe2 112.59(11) . . ?
O3 N9 O2 118.9(2) . . ?
O3 N9 O1 123.1(3) . . ?
O2 N9 O1 118.0(2) . . ?
N8 C14 N7 118.44(16) . . ?
N8 C14 S2 117.98(14) . . ?
N7 C14 S2 123.55(13) . . ?
C14 N8 H9N 120.0 . . ?
C14 N8 H8N 120.0 . . ?
H9N N8 H8N 120.0 . . ?
C14 N7 N6 111.67(14) . . ?
C13 N6 N7 118.85(14) . . ?
C13 N6 Fe2 117.32(12) . . ?
N7 N6 Fe2 123.83(11) . . ?
N1 C5 C4 121.55(16) . . ?
N1 C5 C6 114.23(14) . . ?
C4 C5 C6 124.20(16) . . ?
C3 C4 C5 118.39(19) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C2 C3 C4 119.74(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C2 C1 119.14(19) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C1 C2 122.06(18) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
N5 C8 C9 121.50(18) . . ?
N5 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C10 C9 C8 119.88(19) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.21(19) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C12 118.81(19) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
N5 C12 C11 121.41(17) . . ?
N5 C12 C13 114.14(14) . . ?
C11 C12 C13 124.40(16) . . ?
N6 C13 C12 114.84(15) . . ?
N6 C13 H13 122.6 . . ?
C12 C13 H13 122.6 . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        30.13
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.880
_refine_diff_density_rms         0.267
####################################################################### 
# 
# 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_akhpyac
_database_code_depnum_ccdc_archive 'CCDC 1009328'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2015-03-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H24 Fe N9 O4 S2'
_chemical_formula_sum            'C19 H24 Fe N9 O4 S2'
_chemical_formula_weight         562.44

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                   9.629(5)
_cell_length_b                   10.871(5)
_cell_length_c                   11.758(5)
_cell_angle_alpha                87.529(5)
_cell_angle_beta                 86.832(5)
_cell_angle_gamma                89.597(5)
_cell_volume                     1227.8(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             582
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7325
_exptl_absorpt_correction_T_max  0.8516
_exptl_absorpt_process_details   SADABS(Sheldrick,1997)

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Bruker Smart CCD Area Detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.3
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25695
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         29.93
_reflns_number_total             7027
_reflns_number_gt                6086
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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 > 2σ(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)+(0.0741P)²+0.6426P] 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         7027
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe01 Fe 0.75589(3) 0.44461(2) 0.255301(19) 0.02924(9) Uani 1 1 d . . .
S2 S 0.92502(6) 0.30679(5) 0.26591(4) 0.04052(13) Uani 1 1 d . . .
S1 S 0.58351(6) 0.30993(5) 0.25740(4) 0.03936(12) Uani 1 1 d . . .
N5 N 0.62851(16) 0.57830(15) 0.20585(13) 0.0321(3) Uani 1 1 d . . .
N3 N 0.63424(19) 0.35699(17) 0.47576(14) 0.0399(4) Uani 1 1 d . . .
N6 N 0.79373(16) 0.44155(15) 0.09280(12) 0.0321(3) Uani 1 1 d . . .
N1 N 0.88260(16) 0.57870(15) 0.29416(13) 0.0325(3) Uani 1 1 d . . .
N2 N 0.71852(16) 0.44273(14) 0.41783(12) 0.0305(3) Uani 1 1 d . . .
C13 C 0.63336(19) 0.60048(18) 0.09143(15) 0.0337(4) Uani 1 1 d . . .
N8 N 1.0403(2) 0.2062(2) 0.08350(19) 0.0609(6) Uani 1 1 d . . .
H3N H 1.0568 0.1967 0.0118 0.073 Uiso 1 1 calc R . .
H4N H 1.0830 0.1612 0.1325 0.073 Uiso 1 1 calc R . .
C14 C 0.72772(19) 0.51940(19) 0.02750(14) 0.0335(4) Uani 1 1 d . . .
N7 N 0.88390(19) 0.35896(17) 0.04224(14) 0.0401(4) Uani 1 1 d . . .
C6 C 0.77876(19) 0.52420(18) 0.47616(14) 0.0321(3) Uani 1 1 d . . .
C5 C 0.87289(19) 0.60434(18) 0.40664(15) 0.0330(3) Uani 1 1 d . . .
N4 N 0.4898(3) 0.1970(2) 0.4507(2) 0.0649(6) Uani 1 1 d . . .
H1N H 0.4800 0.1852 0.5235 0.078 Uiso 1 1 calc R . .
H2N H 0.4473 0.1504 0.4068 0.078 Uiso 1 1 calc R . .
C1 C 0.9713(2) 0.6437(2) 0.22315(17) 0.0403(4) Uani 1 1 d . . .
H1 H 0.9767 0.6268 0.1462 0.048 Uiso 1 1 calc R . .
C4 C 0.9519(2) 0.6970(2) 0.44752(19) 0.0437(4) Uani 1 1 d . . .
H4 H 0.9431 0.7155 0.5241 0.052 Uiso 1 1 calc R . .
C8 C 0.5710(2) 0.2877(2) 0.40582(18) 0.0410(4) Uani 1 1 d . . .
C15 C 0.7422(2) 0.5253(2) -0.09938(16) 0.0453(5) Uani 1 1 d . . .
H15C H 0.8089 0.4648 -0.1246 0.068 Uiso 1 1 calc R . .
H15A H 0.7733 0.6058 -0.1257 0.068 Uiso 1 1 calc R . .
H15B H 0.6539 0.5090 -0.1296 0.068 Uiso 1 1 calc R . .
N9 N 0.2728(3) 0.0485(2) 0.2693(3) 0.0706(7) Uani 1 1 d . . .
C9 C 0.5425(2) 0.64455(19) 0.27300(17) 0.0385(4) Uani 1 1 d . . .
H9 H 0.5397 0.6284 0.3514 0.046 Uiso 1 1 calc R . .
C7 C 0.7578(2) 0.5341(2) 0.60150(16) 0.0422(4) Uani 1 1 d . . .
H7A H 0.6921 0.4732 0.6312 0.063 Uiso 1 1 calc R . .
H7B H 0.7228 0.6147 0.6181 0.063 Uiso 1 1 calc R . .
H7C H 0.8448 0.5208 0.6363 0.063 Uiso 1 1 calc R . .
C11 C 0.4627(3) 0.7596(2) 0.1128(2) 0.0530(6) Uani 1 1 d . . .
H11 H 0.4064 0.8207 0.0816 0.064 Uiso 1 1 calc R . .
C12 C 0.5514(2) 0.6920(2) 0.04239(19) 0.0458(5) Uani 1 1 d . . .
H12 H 0.5561 0.7075 -0.0361 0.055 Uiso 1 1 calc R . .
C10 C 0.4580(2) 0.7360(2) 0.2293(2) 0.0478(5) Uani 1 1 d . . .
H10 H 0.3990 0.7809 0.2775 0.057 Uiso 1 1 calc R . .
C16 C 0.9483(2) 0.2909(2) 0.11883(17) 0.0405(4) Uani 1 1 d . . .
C2 C 1.0540(2) 0.7338(2) 0.2603(2) 0.0495(5) Uani 1 1 d . . .
H2 H 1.1164 0.7757 0.2096 0.059 Uiso 1 1 calc R . .
O4 O 0.8121(4) -0.1485(3) 0.1411(3) 0.1185(12) Uani 1 1 d . . .
O3 O 0.3491(4) -0.0015(3) 0.3384(3) 0.1155(12) Uani 1 1 d . . .
O1 O 0.2137(5) -0.0060(3) 0.2000(3) 0.1346(14) Uani 1 1 d . . .
C3 C 1.0440(3) 0.7618(2) 0.3735(2) 0.0507(5) Uani 1 1 d . . .
H3 H 1.0986 0.8236 0.3999 0.061 Uiso 1 1 calc R . .
O2 O 0.2562(5) 0.1586(3) 0.2701(4) 0.1543(18) Uani 1 1 d . . .
C17 C 0.7399(5) -0.0344(4) 0.2959(4) 0.0968(12) Uani 1 1 d . . .
H17A H 0.7890 -0.0975 0.3371 0.145 Uiso 1 1 calc R . .
H17B H 0.6431 -0.0368 0.3200 0.145 Uiso 1 1 calc R . .
H17C H 0.7772 0.0447 0.3106 0.145 Uiso 1 1 calc R . .
C18 C 0.7558(4) -0.0547(3) 0.1748(3) 0.0740(8) Uani 1 1 d . . .
C19 C 0.6910(6) 0.0294(4) 0.0935(4) 0.1119(16) Uani 1 1 d . . .
H19A H 0.7094 0.0017 0.0177 0.168 Uiso 1 1 calc R . .
H19B H 0.7285 0.1105 0.0986 0.168 Uiso 1 1 calc R . .
H19C H 0.5924 0.0316 0.1105 0.168 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Fe01 N2 1.9242(16) . ?
Fe01 N6 1.9269(17) . ?
Fe01 N5 1.9838(17) . ?
Fe01 N1 1.9915(18) . ?
Fe01 S2 2.2101(10) . ?
Fe01 S1 2.2194(10) . ?
S2 C16 1.747(2) . ?
S1 C8 1.749(2) . ?
N5 C9 1.340(2) . ?
N5 C13 1.355(2) . ?
N3 C8 1.315(3) . ?
N3 N2 1.373(2) . ?
N6 C14 1.304(2) . ?
N6 N7 1.375(2) . ?
N1 C1 1.343(3) . ?
N1 C5 1.361(2) . ?
N2 C6 1.302(2) . ?
C13 C12 1.391(3) . ?
C13 C14 1.462(3) . ?
N8 C16 1.337(3) . ?
C14 C15 1.489(3) . ?
N7 C16 1.319(3) . ?
C6 C5 1.455(3) . ?
C6 C7 1.485(2) . ?
C5 C4 1.385(3) . ?
N4 C8 1.335(3) . ?
C1 C2 1.368(3) . ?
C4 C3 1.382(3) . ?
N9 O1 1.198(4) . ?
N9 O2 1.206(4) . ?
N9 O3 1.232(4) . ?
C9 C10 1.380(3) . ?
C11 C10 1.382(4) . ?
C11 C12 1.386(3) . ?
C2 C3 1.377(4) . ?
O4 C18 1.222(4) . ?
C17 C18 1.450(5) . ?
C18 C19 1.457(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
N2 Fe01 N6 178.40(7) . . ?
N2 Fe01 N5 100.58(7) . . ?
N6 Fe01 N5 80.68(7) . . ?
N2 Fe01 N1 80.39(7) . . ?
N6 Fe01 N1 100.72(7) . . ?
N5 Fe01 N1 85.96(8) . . ?
N2 Fe01 S2 93.61(5) . . ?
N6 Fe01 S2 85.23(5) . . ?
N5 Fe01 S2 164.91(5) . . ?
N1 Fe01 S2 91.41(6) . . ?
N2 Fe01 S1 84.87(5) . . ?
N6 Fe01 S1 94.16(5) . . ?
N5 Fe01 S1 90.27(6) . . ?
N1 Fe01 S1 163.83(5) . . ?
S2 Fe01 S1 96.14(5) . . ?
C16 S2 Fe01 95.36(7) . . ?
C8 S1 Fe01 94.88(7) . . ?
C9 N5 C13 119.65(17) . . ?
C9 N5 Fe01 126.82(13) . . ?
C13 N5 Fe01 113.53(12) . . ?
C8 N3 N2 111.75(16) . . ?
C14 N6 N7 118.45(15) . . ?
C14 N6 Fe01 118.34(12) . . ?
N7 N6 Fe01 123.19(12) . . ?
C1 N1 C5 119.08(17) . . ?
C1 N1 Fe01 127.59(14) . . ?
C5 N1 Fe01 113.32(13) . . ?
C6 N2 N3 118.33(15) . . ?
C6 N2 Fe01 118.66(13) . . ?
N3 N2 Fe01 122.99(12) . . ?
N5 C13 C12 121.03(18) . . ?
N5 C13 C14 114.34(16) . . ?
C12 C13 C14 124.62(18) . . ?
N6 C14 C13 113.08(15) . . ?
N6 C14 C15 124.54(18) . . ?
C13 C14 C15 122.36(17) . . ?
C16 N7 N6 111.53(16) . . ?
N2 C6 C5 113.29(16) . . ?
N2 C6 C7 124.21(18) . . ?
C5 C6 C7 122.48(17) . . ?
N1 C5 C4 120.70(18) . . ?
N1 C5 C6 114.18(16) . . ?
C4 C5 C6 125.08(18) . . ?
N1 C1 C2 122.2(2) . . ?
C3 C4 C5 119.4(2) . . ?
N3 C8 N4 118.2(2) . . ?
N3 C8 S1 123.79(16) . . ?
N4 C8 S1 118.01(17) . . ?
O1 N9 O2 117.4(4) . . ?
O1 N9 O3 123.7(3) . . ?
O2 N9 O3 118.9(3) . . ?
N5 C9 C10 122.02(19) . . ?
C10 C11 C12 119.9(2) . . ?
C11 C12 C13 118.7(2) . . ?
C9 C10 C11 118.7(2) . . ?
N7 C16 N8 119.02(19) . . ?
N7 C16 S2 124.09(15) . . ?
N8 C16 S2 116.87(17) . . ?
C1 C2 C3 119.3(2) . . ?
C2 C3 C4 119.2(2) . . ?
O4 C18 C17 120.2(4) . . ?
O4 C18 C19 119.4(4) . . ?
C17 C18 C19 120.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        29.93
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.927
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.082
