# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1499032'
_audit_update_record             
;
2016-08-13 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 Fe2 N O6 S2'
_chemical_formula_sum            'C16 H9 Fe2 N O6 S2'
_chemical_formula_weight         487.06

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   6.8131(3)
_cell_length_b                   13.5955(6)
_cell_length_c                   37.7352(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3495.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4250
_cell_measurement_theta_min      1.079
_cell_measurement_theta_max      32.100

_exptl_crystal_description       Diamondoid
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.934
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_process_details   '(SADABS; Bruker)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40123
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         1.079
_diffrn_reflns_theta_max         32.100
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5564
_reflns_number_gt                4250
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for windows'
_computing_publication_material  Platon
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+2.4718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5564
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.46035(4) 0.14905(2) 0.08427(2) 0.01152(7) Uani 1 1 d . . . . .
Fe2 Fe 0.47434(4) -0.03468(2) 0.08086(2) 0.01229(7) Uani 1 1 d . . . . .
S3 S 0.72543(7) 0.06086(3) 0.09983(2) 0.01212(10) Uani 1 1 d . . . . .
S4 S 0.29381(7) 0.04709(3) 0.12149(2) 0.01371(10) Uani 1 1 d . . . . .
N1 N 0.5930(2) 0.08796(12) 0.16976(4) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.7594(3) 0.05950(15) 0.14850(5) 0.0154(4) Uani 1 1 d . . . . .
H2A H 0.7978 -0.0064 0.1554 0.018 Uiso 1 1 calc R U . . .
H2B H 0.8677 0.1030 0.1542 0.018 Uiso 1 1 calc R U . . .
C1 C 0.4246(3) 0.02736(15) 0.16418(5) 0.0157(4) Uani 1 1 d . . . . .
H1A H 0.3328 0.0387 0.1834 0.019 Uiso 1 1 calc R U . . .
H1B H 0.4652 -0.0409 0.1654 0.019 Uiso 1 1 calc R U . . .
C7 C 0.7071(3) 0.33444(15) 0.20644(5) 0.0172(4) Uani 1 1 d . . . . .
H7 H 0.8170 0.3717 0.2123 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3587(3) 0.31565(15) 0.20361(5) 0.0175(4) Uani 1 1 d . . . . .
H4 H 0.2331 0.3396 0.2079 0.021 Uiso 1 1 calc R U . . .
C9 C 0.4954(3) 0.47160(16) 0.22623(5) 0.0181(4) Uani 1 1 d . . . . .
C6 C 0.7324(3) 0.24125(15) 0.19250(5) 0.0156(4) Uani 1 1 d . . . . .
H6 H 0.8585 0.2165 0.1894 0.019 Uiso 1 1 calc R U . . .
C8 C 0.5212(3) 0.37380(15) 0.21194(5) 0.0157(4) Uani 1 1 d . . . . .
C10 C 0.4711(3) 0.55109(16) 0.23799(6) 0.0231(5) Uani 1 1 d . . . . .
H10 H 0.4519 0.6137 0.2473 0.028 Uiso 1 1 calc R U . . .
C5 C 0.5696(3) 0.18358(14) 0.18296(5) 0.0139(4) Uani 1 1 d . . . . .
C3 C 0.3818(3) 0.22269(15) 0.18910(5) 0.0163(4) Uani 1 1 d . . . . .
H3 H 0.2714 0.1857 0.1834 0.020 Uiso 1 1 calc R U . . .
C13 C 0.4930(3) 0.26602(15) 0.10633(5) 0.0159(4) Uani 1 1 d . . . . .
C11 C 0.2287(3) 0.17115(14) 0.06240(5) 0.0154(4) Uani 1 1 d . . . . .
C12 C 0.5878(3) 0.17997(15) 0.04414(5) 0.0167(4) Uani 1 1 d . . . . .
O3 O 0.5159(2) 0.34179(11) 0.11871(4) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.6674(2) 0.19805(12) 0.01842(4) 0.0268(4) Uani 1 1 d . . . . .
O1 O 0.0852(2) 0.18412(12) 0.04795(4) 0.0231(3) Uani 1 1 d . . . . .
O6 O 0.5215(2) -0.21862(11) 0.12087(4) 0.0261(4) Uani 1 1 d . . . . .
O5 O 0.6969(2) -0.07269(13) 0.01546(4) 0.0286(4) Uani 1 1 d . . . . .
O4 O 0.1101(2) -0.07941(12) 0.04235(4) 0.0261(4) Uani 1 1 d . . . . .
C16 C 0.2502(3) -0.06216(15) 0.05725(5) 0.0167(4) Uani 1 1 d . . . . .
C14 C 0.5068(3) -0.14806(15) 0.10454(5) 0.0170(4) Uani 1 1 d . . . . .
C15 C 0.6139(3) -0.05883(15) 0.04117(5) 0.0175(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C12 1.795(2) . ?
Fe1 C11 1.806(2) . ?
Fe1 C13 1.809(2) . ?
Fe1 S3 2.2459(5) . ?
Fe1 S4 2.2764(5) . ?
Fe1 Fe2 2.5030(4) . ?
Fe2 C14 1.795(2) . ?
Fe2 C15 1.804(2) . ?
Fe2 C16 1.807(2) . ?
Fe2 S4 2.2583(6) . ?
Fe2 S3 2.2641(5) . ?
S3 C2 1.8511(19) . ?
S4 C1 1.860(2) . ?
N1 C5 1.401(2) . ?
N1 C1 1.428(3) . ?
N1 C2 1.441(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C7 C6 1.383(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9300 . ?
C4 C3 1.386(3) . ?
C4 C8 1.396(3) . ?
C4 H4 0.9300 . ?
C9 C10 1.180(3) . ?
C9 C8 1.446(3) . ?
C6 C5 1.405(3) . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C5 C3 1.405(3) . ?
C3 H3 0.9300 . ?
C13 O3 1.142(2) . ?
C11 O1 1.133(2) . ?
C12 O2 1.139(2) . ?
O6 C14 1.144(2) . ?
O5 C15 1.139(3) . ?
O4 C16 1.132(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Fe1 C11 89.91(9) . . ?
C12 Fe1 C13 97.05(9) . . ?
C11 Fe1 C13 99.88(9) . . ?
C12 Fe1 S3 87.51(6) . . ?
C11 Fe1 S3 155.64(6) . . ?
C13 Fe1 S3 104.48(6) . . ?
C12 Fe1 S4 154.70(7) . . ?
C11 Fe1 S4 87.00(6) . . ?
C13 Fe1 S4 108.23(6) . . ?
S3 Fe1 S4 85.091(19) . . ?
C12 Fe1 Fe2 99.90(7) . . ?
C11 Fe1 Fe2 100.12(6) . . ?
C13 Fe1 Fe2 153.69(6) . . ?
S3 Fe1 Fe2 56.638(15) . . ?
S4 Fe1 Fe2 56.153(15) . . ?
C14 Fe2 C15 101.08(9) . . ?
C14 Fe2 C16 99.89(9) . . ?
C15 Fe2 C16 89.91(9) . . ?
C14 Fe2 S4 98.73(7) . . ?
C15 Fe2 S4 160.10(7) . . ?
C16 Fe2 S4 88.64(7) . . ?
C14 Fe2 S3 104.02(6) . . ?
C15 Fe2 S3 88.21(7) . . ?
C16 Fe2 S3 155.93(7) . . ?
S4 Fe2 S3 85.090(19) . . ?
C14 Fe2 Fe1 146.71(6) . . ?
C15 Fe2 Fe1 104.15(7) . . ?
C16 Fe2 Fe1 101.51(7) . . ?
S4 Fe2 Fe1 56.844(15) . . ?
S3 Fe2 Fe1 55.944(15) . . ?
C2 S3 Fe1 111.42(7) . . ?
C2 S3 Fe2 113.72(7) . . ?
Fe1 S3 Fe2 67.419(17) . . ?
C1 S4 Fe2 104.84(7) . . ?
C1 S4 Fe1 112.55(7) . . ?
Fe2 S4 Fe1 67.003(17) . . ?
C5 N1 C1 119.74(17) . . ?
C5 N1 C2 122.44(17) . . ?
C1 N1 C2 113.25(16) . . ?
N1 C2 S3 116.82(13) . . ?
N1 C2 H2A 108.1 . . ?
S3 C2 H2A 108.1 . . ?
N1 C2 H2B 108.1 . . ?
S3 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
N1 C1 S4 115.42(13) . . ?
N1 C1 H1A 108.4 . . ?
S4 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
S4 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
C6 C7 C8 121.53(19) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C3 C4 C8 121.01(19) . . ?
C3 C4 H4 119.5 . . ?
C8 C4 H4 119.5 . . ?
C10 C9 C8 178.9(2) . . ?
C7 C6 C5 120.68(19) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C7 C8 C4 118.09(18) . . ?
C7 C8 C9 121.36(19) . . ?
C4 C8 C9 120.55(19) . . ?
C9 C10 H10 180.0 . . ?
N1 C5 C3 120.89(18) . . ?
N1 C5 C6 121.25(18) . . ?
C3 C5 C6 117.74(18) . . ?
C4 C3 C5 120.89(19) . . ?
C4 C3 H3 119.6 . . ?
C5 C3 H3 119.6 . . ?
O3 C13 Fe1 176.70(18) . . ?
O1 C11 Fe1 178.34(18) . . ?
O2 C12 Fe1 178.7(2) . . ?
O4 C16 Fe2 179.8(2) . . ?
O6 C14 Fe2 176.69(19) . . ?
O5 C15 Fe2 177.66(19) . . ?

_refine_diff_density_max         0.530
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.103


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       ', '
