# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_E108

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H8 Mn2 O6 S4'
_chemical_formula_weight         558.36

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'
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'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.5196(18)
_cell_length_b                   12.168(2)
_cell_length_c                   16.446(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.987(4)
_cell_angle_gamma                90
_cell_volume                     2097.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    975
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.50

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.636
_shelx_estimated_absorpt_T_min   0.440
_shelx_estimated_absorpt_T_max   0.736
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17431
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.085
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4816
_reflns_number_gt                4439
_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 SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0333P)²+1.3571P] 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         4816
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Mn1 Mn 0.45373(3) 0.24708(2) 1.08841(2) 0.01187(7) Uani 1 1 d . . . . .
Mn2 Mn 0.23137(3) 0.16256(2) 0.93604(2) 0.01204(7) Uani 1 1 d . . . . .
S1 S 0.36354(4) 0.40291(3) 1.02835(2) 0.01174(9) Uani 1 1 d . . . . .
S2 S 0.23924(4) 0.18626(4) 1.08179(3) 0.01351(10) Uani 1 1 d . . . . .
S3 S 0.28442(4) 0.34171(4) 0.90819(2) 0.01158(9) Uani 1 1 d . . . . .
S4 S 0.45488(4) 0.14300(4) 0.96398(3) 0.01299(10) Uani 1 1 d . . . . .
O1 O 0.43764(14) 0.34769(11) 1.25024(8) 0.0203(3) Uani 1 1 d . . . . .
O2 O 0.71491(14) 0.32756(13) 1.06834(9) 0.0249(3) Uani 1 1 d . . . . .
O3 O 0.55877(16) 0.05439(13) 1.18193(9) 0.0303(4) Uani 1 1 d . . . . .
O4 O -0.04678(14) 0.20634(13) 0.92686(8) 0.0248(3) Uani 1 1 d . . . . .
O5 O 0.23076(13) 0.12065(12) 0.75907(8) 0.0207(3) Uani 1 1 d . . . . .
O6 O 0.19164(17) -0.07677(13) 0.95627(10) 0.0344(4) Uani 1 1 d . . . . .
C1 C 0.21491(17) 0.41082(15) 1.07074(10) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.15555(17) 0.51180(16) 1.07855(10) 0.0152(4) Uani 1 1 d . . . . .
H2 H 0.1930 0.5773 1.0601 0.018 Uiso 1 1 calc R U . . .
C3 C 0.04039(18) 0.51509(17) 1.11386(11) 0.0194(4) Uani 1 1 d . . . . .
H3 H 0.0001 0.5837 1.1218 0.023 Uiso 1 1 calc R U . . .
C4 C -0.01620(18) 0.41837(17) 1.13764(11) 0.0191(4) Uani 1 1 d . . . . .
H4 H -0.0951 0.4216 1.1616 0.023 Uiso 1 1 calc R U . . .
C5 C 0.04082(18) 0.31734(17) 1.12684(11) 0.0175(4) Uani 1 1 d . . . . .
H5 H -0.0003 0.2516 1.1415 0.021 Uiso 1 1 calc R U . . .
C6 C 0.15922(17) 0.31265(15) 1.09419(10) 0.0134(3) Uani 1 1 d . . . . .
C7 C 0.43365(17) 0.32668(15) 0.86701(10) 0.0128(3) Uani 1 1 d . . . . .
C8 C 0.47428(18) 0.40436(15) 0.81272(10) 0.0153(4) Uani 1 1 d . . . . .
H8 H 0.4221 0.4657 0.7967 0.018 Uiso 1 1 calc R U . . .
C9 C 0.59242(19) 0.39057(16) 0.78233(11) 0.0175(4) Uani 1 1 d . . . . .
H9 H 0.6211 0.4420 0.7445 0.021 Uiso 1 1 calc R U . . .
C10 C 0.66879(18) 0.30099(16) 0.80754(11) 0.0183(4) Uani 1 1 d . . . . .
H10 H 0.7493 0.2918 0.7864 0.022 Uiso 1 1 calc R U . . .
C11 C 0.62919(18) 0.22526(16) 0.86291(11) 0.0161(4) Uani 1 1 d . . . . .
H11 H 0.6829 0.1655 0.8803 0.019 Uiso 1 1 calc R U . . .
C12 C 0.51014(17) 0.23719(14) 0.89298(10) 0.0126(3) Uani 1 1 d . . . . .
C13 C 0.44365(17) 0.31113(15) 1.18633(11) 0.0147(4) Uani 1 1 d . . . . .
C14 C 0.61440(19) 0.29685(16) 1.07688(10) 0.0162(4) Uani 1 1 d . . . . .
C15 C 0.51706(19) 0.12566(17) 1.14351(11) 0.0193(4) Uani 1 1 d . . . . .
C16 C 0.06047(19) 0.18947(16) 0.92907(11) 0.0165(4) Uani 1 1 d . . . . .
C17 C 0.23262(17) 0.13745(15) 0.82806(11) 0.0154(4) Uani 1 1 d . . . . .
C18 C 0.20623(19) 0.01572(17) 0.95078(11) 0.0206(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
Mn1 C13 1.8005(19) . ?
Mn1 C14 1.821(2) . ?
Mn1 C15 1.828(2) . ?
Mn1 S1 2.3038(6) . ?
Mn1 S2 2.3682(6) . ?
Mn1 S4 2.4074(6) . ?
Mn2 C17 1.8032(19) . ?
Mn2 C16 1.821(2) . ?
Mn2 C18 1.825(2) . ?
Mn2 S3 2.3059(6) . ?
Mn2 S4 2.3682(6) . ?
Mn2 S2 2.4085(7) . ?
S1 C1 1.7690(19) . ?
S1 S3 2.2061(7) . ?
S2 C6 1.7734(19) . ?
S3 C7 1.7724(19) . ?
S4 C12 1.7700(18) . ?
O1 C13 1.148(2) . ?
O2 C14 1.141(2) . ?
O3 C15 1.138(2) . ?
O4 C16 1.144(2) . ?
O5 C17 1.151(2) . ?
O6 C18 1.140(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.399(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(3) . ?
C5 H5 0.9500 . ?
C7 C8 1.393(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.396(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11 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
C13 Mn1 C14 94.39(8) . . ?
C13 Mn1 C15 87.34(8) . . ?
C14 Mn1 C15 91.08(9) . . ?
C13 Mn1 S1 88.46(6) . . ?
C14 Mn1 S1 91.90(6) . . ?
C15 Mn1 S1 175.03(6) . . ?
C13 Mn1 S2 92.66(6) . . ?
C14 Mn1 S2 171.32(6) . . ?
C15 Mn1 S2 94.30(7) . . ?
S1 Mn1 S2 83.24(2) . . ?
C13 Mn1 S4 173.22(6) . . ?
C14 Mn1 S4 90.75(6) . . ?
C15 Mn1 S4 88.15(6) . . ?
S1 Mn1 S4 95.79(2) . . ?
S2 Mn1 S4 82.631(18) . . ?
C17 Mn2 C16 93.45(8) . . ?
C17 Mn2 C18 88.77(8) . . ?
C16 Mn2 C18 91.76(9) . . ?
C17 Mn2 S3 86.67(6) . . ?
C16 Mn2 S3 94.14(6) . . ?
C18 Mn2 S3 172.74(7) . . ?
C17 Mn2 S4 94.70(6) . . ?
C16 Mn2 S4 171.23(6) . . ?
C18 Mn2 S4 91.65(7) . . ?
S3 Mn2 S4 83.118(18) . . ?
C17 Mn2 S2 176.27(6) . . ?
C16 Mn2 S2 89.39(6) . . ?
C18 Mn2 S2 88.74(6) . . ?
S3 Mn2 S2 95.541(18) . . ?
S4 Mn2 S2 82.605(18) . . ?
C1 S1 S3 95.39(6) . . ?
C1 S1 Mn1 102.77(6) . . ?
S3 S1 Mn1 102.44(2) . . ?
C6 S2 Mn1 100.58(6) . . ?
C6 S2 Mn2 104.05(6) . . ?
Mn1 S2 Mn2 91.909(18) . . ?
C7 S3 S1 95.70(6) . . ?
C7 S3 Mn2 102.48(6) . . ?
S1 S3 Mn2 102.71(2) . . ?
C12 S4 Mn2 100.62(6) . . ?
C12 S4 Mn1 104.27(6) . . ?
Mn2 S4 Mn1 91.937(18) . . ?
C2 C1 C6 121.82(17) . . ?
C2 C1 S1 120.29(14) . . ?
C6 C1 S1 117.88(14) . . ?
C3 C2 C1 118.66(18) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.24(18) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 120.93(18) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.65(18) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 118.60(17) . . ?
C1 C6 S2 119.63(14) . . ?
C5 C6 S2 121.77(14) . . ?
C8 C7 C12 121.58(17) . . ?
C8 C7 S3 120.42(14) . . ?
C12 C7 S3 117.96(13) . . ?
C9 C8 C7 118.86(17) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.82(17) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 121.11(18) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.68(17) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C7 118.93(16) . . ?
C11 C12 S4 121.57(14) . . ?
C7 C12 S4 119.50(14) . . ?
O1 C13 Mn1 177.13(16) . . ?
O2 C14 Mn1 178.88(16) . . ?
O3 C15 Mn1 175.60(18) . . ?
O4 C16 Mn2 178.22(16) . . ?
O5 C17 Mn2 178.53(17) . . ?
O6 C18 Mn2 176.80(18) . . ?

_refine_diff_density_max         0.504
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1025148'
