# 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_mm355a
_database_code_depnum_ccdc_archive 'CCDC 1021206'
_audit_update_record             
;
2014-08-26 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Cl2 Fe N5 S'
_chemical_formula_sum            'C12 H8 Cl2 Fe N5 S'
_chemical_formula_weight         381.04

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'
Cl Cl 0.1484 0.1585 '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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

_cell_length_a                   13.7473(4)
_cell_length_b                   7.1687(2)
_cell_length_c                   14.4831(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1427.31(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.29

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.575
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with three batch runs at phi = 0.00 deg 
 (650 frames), at phi = 120.00 deg (650 frames), and at phi = 240.00 deg 
 (650 frames). 
 Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18203
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.042
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             1890
_reflns_number_gt                1803
_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0397P)²+0.3011P] 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         1890
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0218
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0590
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.79405(2) 0.2500 0.42677(2) 0.01786(8) Uani 1 2 d S T P . .
Cl1 Cl 0.88236(2) 0.50483(4) 0.40681(2) 0.02966(9) Uani 1 1 d . . . . .
S1 S 0.44649(3) 0.2500 0.51453(3) 0.04244(14) Uani 1 2 d S T P . .
N1 N 0.65514(9) 0.2500 0.46162(9) 0.0231(3) Uani 1 2 d S T P . .
N2 N 0.54170(11) 0.2500 0.58801(10) 0.0320(3) Uani 1 2 d S T P . .
N3 N 0.49035(11) 0.2500 0.40588(10) 0.0318(3) Uani 1 2 d S T P . .
N4 N 0.79913(9) 0.2500 0.57339(8) 0.0215(3) Uani 1 2 d S T P . .
N5 N 0.72143(9) 0.2500 0.29635(9) 0.0213(2) Uani 1 2 d S T P . .
C1 C 0.62757(11) 0.2500 0.55380(10) 0.0231(3) Uani 1 2 d S T P . .
C2 C 0.58305(11) 0.2500 0.39486(10) 0.0229(3) Uani 1 2 d S T P . .
C3 C 0.71244(11) 0.2500 0.61664(10) 0.0213(3) Uani 1 2 d S T P . .
C4 C 0.70540(12) 0.2500 0.71231(11) 0.0285(3) Uani 1 2 d S T P . .
H4A H 0.6437 0.2500 0.7418 0.034 Uiso 1 2 calc R U P . .
C5 C 0.79020(13) 0.2500 0.76370(11) 0.0314(4) Uani 1 2 d S T P . .
H5A H 0.7873 0.2500 0.8292 0.038 Uiso 1 2 calc R U P . .
C6 C 0.87926(13) 0.2500 0.71924(12) 0.0307(4) Uani 1 2 d S T P . .
H6A H 0.9381 0.2500 0.7537 0.037 Uiso 1 2 calc R U P . .
C7 C 0.88115(12) 0.2500 0.62335(11) 0.0288(3) Uani 1 2 d S T P . .
H7A H 0.9421 0.2500 0.5924 0.035 Uiso 1 2 calc R U P . .
C8 C 0.62343(11) 0.2500 0.30029(10) 0.0211(3) Uani 1 2 d S T P . .
C9 C 0.56672(12) 0.2500 0.22120(11) 0.0306(4) Uani 1 2 d S T P . .
H9A H 0.4978 0.2500 0.2255 0.037 Uiso 1 2 calc R U P . .
C10 C 0.61190(12) 0.2500 0.13598(11) 0.0316(4) Uani 1 2 d S T P . .
H10A H 0.5744 0.2500 0.0809 0.038 Uiso 1 2 calc R U P . .
C11 C 0.71236(12) 0.2500 0.13192(11) 0.0298(4) Uani 1 2 d S T P . .
H11A H 0.7448 0.2500 0.0740 0.036 Uiso 1 2 calc R U P . .
C12 C 0.76490(12) 0.2500 0.21331(11) 0.0279(3) Uani 1 2 d S T P . .
H12A H 0.8339 0.2500 0.2104 0.033 Uiso 1 2 calc R U 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
Fe1 N1 1.9751(13) . ?
Fe1 N4 2.1246(12) . ?
Fe1 N5 2.1364(13) . ?
Fe1 Cl1 2.2124(3) . ?
Fe1 Cl1 2.2124(3) 7_565 ?
S1 N3 1.6852(15) . ?
S1 N2 1.6869(16) . ?
N1 C2 1.3847(19) . ?
N1 C1 1.3878(19) . ?
N2 C1 1.280(2) . ?
N3 C2 1.284(2) . ?
N4 C7 1.340(2) . ?
N4 C3 1.3463(19) . ?
N5 C12 1.343(2) . ?
N5 C8 1.3484(19) . ?
C1 C3 1.480(2) . ?
C2 C8 1.478(2) . ?
C3 C4 1.389(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.383(2) . ?
C6 C7 1.389(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.382(2) . ?
C10 C11 1.382(2) . ?
C11 C12 1.383(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
N1 Fe1 N4 77.08(5) . . ?
N1 Fe1 N5 76.95(5) . . ?
N4 Fe1 N5 154.03(5) . . ?
N1 Fe1 Cl1 124.328(9) . . ?
N4 Fe1 Cl1 96.46(2) . . ?
N5 Fe1 Cl1 98.10(2) . . ?
N1 Fe1 Cl1 124.329(9) . 7_565 ?
N4 Fe1 Cl1 96.46(2) . 7_565 ?
N5 Fe1 Cl1 98.10(2) . 7_565 ?
Cl1 Fe1 Cl1 111.319(19) . 7_565 ?
N3 S1 N2 108.15(7) . . ?
C2 N1 C1 118.44(13) . . ?
C2 N1 Fe1 120.90(10) . . ?
C1 N1 Fe1 120.66(10) . . ?
C1 N2 S1 118.12(12) . . ?
C2 N3 S1 118.10(12) . . ?
C7 N4 C3 119.58(14) . . ?
C7 N4 Fe1 124.57(11) . . ?
C3 N4 Fe1 115.85(10) . . ?
C12 N5 C8 118.85(13) . . ?
C12 N5 Fe1 125.72(10) . . ?
C8 N5 Fe1 115.43(10) . . ?
N2 C1 N1 128.62(15) . . ?
N2 C1 C3 119.27(14) . . ?
N1 C1 C3 112.11(13) . . ?
N3 C2 N1 128.57(14) . . ?
N3 C2 C8 119.20(13) . . ?
N1 C2 C8 112.23(13) . . ?
N4 C3 C4 121.73(14) . . ?
N4 C3 C1 114.31(13) . . ?
C4 C3 C1 123.96(14) . . ?
C5 C4 C3 118.56(15) . . ?
C4 C5 C6 119.70(16) . . ?
C5 C6 C7 118.81(16) . . ?
N4 C7 C6 121.62(16) . . ?
N5 C8 C9 121.81(14) . . ?
N5 C8 C2 114.49(12) . . ?
C9 C8 C2 123.70(14) . . ?
C10 C9 C8 119.05(15) . . ?
C9 C10 C11 119.15(15) . . ?
C10 C11 C12 119.05(15) . . ?
N5 C12 C11 122.08(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 S1 N2 C1 0.000(0) . . . . ?
N2 S1 N3 C2 0.000(0) . . . . ?
S1 N2 C1 N1 0.000(0) . . . . ?
S1 N2 C1 C3 180.000(0) . . . . ?
C2 N1 C1 N2 0.000(0) . . . . ?
Fe1 N1 C1 N2 180.000(0) . . . . ?
C2 N1 C1 C3 180.000(0) . . . . ?
Fe1 N1 C1 C3 0.000(0) . . . . ?
S1 N3 C2 N1 0.000(0) . . . . ?
S1 N3 C2 C8 180.000(0) . . . . ?
C1 N1 C2 N3 0.000(0) . . . . ?
Fe1 N1 C2 N3 180.000(0) . . . . ?
C1 N1 C2 C8 180.000(0) . . . . ?
Fe1 N1 C2 C8 0.000(0) . . . . ?
C7 N4 C3 C4 0.000(0) . . . . ?
Fe1 N4 C3 C4 180.000(0) . . . . ?
C7 N4 C3 C1 180.000(0) . . . . ?
Fe1 N4 C3 C1 0.000(0) . . . . ?
N2 C1 C3 N4 180.000(0) . . . . ?
N1 C1 C3 N4 0.000(0) . . . . ?
N2 C1 C3 C4 0.000(0) . . . . ?
N1 C1 C3 C4 180.000(0) . . . . ?
N4 C3 C4 C5 0.000(0) . . . . ?
C1 C3 C4 C5 180.000(0) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 C7 0.000(0) . . . . ?
C3 N4 C7 C6 0.000(0) . . . . ?
Fe1 N4 C7 C6 180.000(0) . . . . ?
C5 C6 C7 N4 0.000(0) . . . . ?
C12 N5 C8 C9 0.000(0) . . . . ?
Fe1 N5 C8 C9 180.000(0) . . . . ?
C12 N5 C8 C2 180.000(0) . . . . ?
Fe1 N5 C8 C2 0.000(0) . . . . ?
N3 C2 C8 N5 180.000(0) . . . . ?
N1 C2 C8 N5 0.000(0) . . . . ?
N3 C2 C8 C9 0.000(0) . . . . ?
N1 C2 C8 C9 180.000(0) . . . . ?
N5 C8 C9 C10 0.000(0) . . . . ?
C2 C8 C9 C10 180.000(0) . . . . ?
C8 C9 C10 C11 0.000(0) . . . . ?
C9 C10 C11 C12 0.000(0) . . . . ?
C8 N5 C12 C11 0.000(0) . . . . ?
Fe1 N5 C12 C11 180.000(0) . . . . ?
C10 C11 C12 N5 0.000(0) . . . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-4

