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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_struct

_audit_creation_date             2006-10-12T16:32:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H36 Mn2 N2 O18 S2'
_chemical_formula_sum            'C20 H36 Mn2 N2 O18 S2'
_chemical_formula_weight         766.51
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.160(5)
_cell_length_b                   21.760(5)
_cell_length_c                   17.609(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     3127(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    180
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      3
_cell_measurement_theta_max      26
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'pale green'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.015
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1584
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0773
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_number            24786
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.2
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_full        26.03
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             6098
_reflns_number_gt                4405
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'IPDS (Stoe & Cie, 1996)'
_computing_cell_refinement       'IPDS (Stoe & Cie, 1996)'
_computing_data_reduction        'XRED (Stoe & Cie 1996)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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.
Hydrogen atoms could not be located on water molecules
;
_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)+(0.1029P)²+0.0000P] 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_number_reflns         6098
_refine_ls_number_parameters     376
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.165
_refine_ls_wR_factor_gt          0.143
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.45(3)
_refine_diff_density_max         1.179
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.122

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_number_in_cell
C 80
H 144
Mn 8
N 8
O 72
S 8

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
C1 C 0.3536(8) 0.8857(3) 0.8423(4) 0.0236(14) Uani 1 1 d . . .
C2 C 0.3573(9) 0.9065(3) 0.9180(4) 0.0309(15) Uani 1 1 d . . .
H2 H 0.4197 0.8859 0.9542 0.037 Uiso 1 1 calc R . .
C3 C 0.2667(9) 0.9580(3) 0.9379(4) 0.0322(16) Uani 1 1 d . . .
H3 H 0.2682 0.9713 0.9881 0.039 Uiso 1 1 calc R . .
C4 C 0.1733(8) 0.9905(3) 0.8849(4) 0.0254(14) Uani 1 1 d . . .
C5 C 0.1702(8) 0.9695(3) 0.8106(4) 0.0269(14) Uani 1 1 d . . .
H5 H 0.1078 0.9906 0.7749 0.032 Uiso 1 1 calc R . .
C6 C 0.2581(8) 0.9177(3) 0.7877(4) 0.0254(14) Uani 1 1 d . . .
C7 C 0.2585(8) 0.9021(3) 0.7089(4) 0.0271(14) Uani 1 1 d . . .
H7 H 0.2101 0.93 0.6759 0.033 Uiso 1 1 calc R . .
C8 C 0.3209(9) 0.8482(3) 0.5959(4) 0.0288(14) Uani 1 1 d . . .
H8A H 0.4316 0.8546 0.5775 0.035 Uiso 1 1 calc R . .
H8B H 0.2523 0.8805 0.5753 0.035 Uiso 1 1 calc R . .
C9 C 0.2589(9) 0.7862(3) 0.5674(4) 0.0258(14) Uani 1 1 d . . .
H9A H 0.1534 0.778 0.5907 0.031 Uiso 1 1 calc R . .
H9B H 0.2414 0.7891 0.513 0.031 Uiso 1 1 calc R . .
C10 C 0.3704(8) 0.7321(3) 0.5827(3) 0.0236(14) Uani 1 1 d . . .
H10 H 0.4796 0.7413 0.5625 0.028 Uiso 1 1 calc R . .
C11 C 0.3068(9) 0.6738(3) 0.5453(4) 0.0265(14) Uani 1 1 d . . .
H11A H 0.2901 0.6818 0.4916 0.032 Uiso 1 1 calc R . .
H11B H 0.201 0.6637 0.5671 0.032 Uiso 1 1 calc R . .
C12 C 0.4197(9) 0.6182(3) 0.5535(4) 0.0282(14) Uani 1 1 d . . .
H12A H 0.3836 0.586 0.5193 0.034 Uiso 1 1 calc R . .
H12B H 0.5302 0.6298 0.5391 0.034 Uiso 1 1 calc R . .
C13 C 0.3840(9) 0.5366(3) 0.6427(4) 0.0287(15) Uani 1 1 d . . .
H13 H 0.3605 0.5132 0.5999 0.034 Uiso 1 1 calc R . .
C14 C 0.3765(8) 0.5066(3) 0.7150(4) 0.0261(14) Uani 1 1 d . . .
C15 C 0.3026(9) 0.4484(3) 0.7191(4) 0.0323(16) Uani 1 1 d . . .
H15 H 0.2611 0.4301 0.6754 0.039 Uiso 1 1 calc R . .
C16 C 0.2917(9) 0.4184(3) 0.7873(4) 0.0290(14) Uani 1 1 d . . .
C17 C 0.3555(9) 0.4446(3) 0.8531(4) 0.0289(15) Uani 1 1 d . . .
H17 H 0.3457 0.4242 0.8993 0.035 Uiso 1 1 calc R . .
C18 C 0.4335(10) 0.5011(3) 0.8500(4) 0.0334(16) Uani 1 1 d . . .
H18 H 0.4772 0.5181 0.894 0.04 Uiso 1 1 calc R . .
C19 C 0.4469(8) 0.5326(3) 0.7810(4) 0.0273(14) Uani 1 1 d . . .
C20b C 0.501(6) 0.705(3) 0.8784(12) 0.077(6) Uani 0.3 1 d PD A 1
H20A H 0.605 0.7235 0.8948 0.115 Uiso 0.3 1 d P B 1
H20B H 0.4142 0.7241 0.9054 0.115 Uiso 0.3 1 d P C 1
H20C H 0.5059 0.6618 0.8909 0.115 Uiso 0.3 1 d P D 1
C20a C 0.587(2) 0.7076(11) 0.8615(10) 0.077(6) Uani 0.7 1 d PD A 2
H21A H 0.5699 0.668 0.8848 0.115 Uiso 0.7 1 d P E 2
H21B H 0.6988 0.7119 0.847 0.115 Uiso 0.7 1 d P F 2
H21C H 0.5586 0.7392 0.8977 0.115 Uiso 0.7 1 d P G 2
Mn1 Mn 0.41330(13) 0.78554(4) 0.74146(6) 0.0254(2) Uani 1 1 d . . .
Mn2 Mn 0.46206(12) 0.65154(4) 0.71788(6) 0.0254(2) Uani 1 1 d . A .
N1 N 0.3203(7) 0.8523(3) 0.6788(3) 0.0269(12) Uani 1 1 d . . .
N2 N 0.4211(7) 0.5943(3) 0.6321(3) 0.0266(12) Uani 1 1 d . . .
O1 O 0.4445(6) 0.8366(2) 0.8242(3) 0.0302(11) Uani 1 1 d . . .
O2 O 0.3830(6) 0.7233(2) 0.6641(2) 0.0279(10) Uani 1 1 d . . .
O3 O 0.5270(6) 0.5865(2) 0.7794(3) 0.0309(11) Uani 1 1 d . . .
O4 O 0.4822(6) 0.7131(2) 0.7956(3) 0.0294(10) Uani 1 1 d D . .
O5 O 0.1914(6) 0.6386(2) 0.7568(3) 0.0317(11) Uani 1 1 d . . .
O6 O 0.7136(6) 0.6737(2) 0.6825(3) 0.0406(13) Uani 1 1 d . . .
O7 O 0.1556(6) 0.7632(2) 0.7857(3) 0.0335(11) Uani 1 1 d . . .
O8 O -0.0376(7) 1.0378(2) 0.9760(3) 0.0398(13) Uani 1 1 d . . .
O9 O -0.0375(6) 1.0711(2) 0.8450(3) 0.0361(12) Uani 1 1 d . . .
O10 O 0.1781(6) 1.1033(2) 0.9315(3) 0.0328(11) Uani 1 1 d . . .
O11 O 0.1248(7) 0.3314(2) 0.7220(3) 0.0412(13) Uani 1 1 d . . .
O12 O 0.3369(6) 0.3021(2) 0.8109(3) 0.0309(11) Uani 1 1 d . . .
O13 O 0.0872(6) 0.3462(3) 0.8573(3) 0.0409(12) Uani 1 1 d . . .
O14 O 0.8217(13) 0.5451(5) 0.8653(6) 0.096(3) Uiso 1 1 d . . .
O15 O 0.1035(8) 0.6156(3) 0.9025(4) 0.0566(16) Uiso 1 1 d . . .
O16 O 0.2881(9) 0.5715(3) 1.0180(4) 0.0574(16) Uiso 1 1 d . . .
O17 O 0.1585(12) 0.7394(4) 0.9450(5) 0.090(3) Uiso 1 1 d . . .
O18 O 0.8732(13) 0.8087(4) 0.9385(5) 0.095(3) Uiso 1 1 d . . .
S1 S 0.0603(2) 1.05541(7) 0.91118(9) 0.0262(4) Uani 1 1 d . . .
S2 S 0.2015(2) 0.34507(8) 0.79473(11) 0.0303(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.339(8) . ?
C1 C2 1.408(10) . ?
C1 C6 1.421(9) . ?
C2 C3 1.388(9) . ?
C3 C4 1.397(10) . ?
C4 C5 1.387(10) . ?
C4 S1 1.749(7) . ?
C5 C6 1.395(9) . ?
C6 C7 1.429(10) . ?
C7 N1 1.307(9) . ?
C8 N1 1.463(8) . ?
C8 C9 1.526(9) . ?
C9 C10 1.512(9) . ?
C10 O2 1.449(8) . ?
C10 C11 1.521(9) . ?
C11 C12 1.527(9) . ?
C12 N2 1.478(8) . ?
C13 N2 1.305(9) . ?
C13 C14 1.433(10) . ?
C14 C15 1.406(9) . ?
C14 C19 1.414(10) . ?
C15 C16 1.370(10) . ?
C16 C17 1.393(10) . ?
C16 S2 1.762(7) . ?
C17 C18 1.385(10) . ?
C18 C19 1.400(10) . ?
C19 O3 1.343(8) . ?
C20b O4 1.48(2) . ?
C20a O4 1.447(13) . ?
Mn1 O1 1.849(5) . ?
Mn1 O4 1.926(5) . ?
Mn1 O2 1.938(5) . ?
Mn1 N1 1.975(6) . ?
Mn1 O12 2.266(5) 3_656 ?
Mn1 O7 2.295(5) . ?
Mn1 Mn2 2.9721(15) . ?
Mn2 O3 1.858(5) . ?
Mn2 O4 1.923(5) . ?
Mn2 O2 1.937(5) . ?
Mn2 N2 1.985(6) . ?
Mn2 O6 2.198(6) . ?
Mn2 O5 2.329(5) . ?
O8 S1 1.445(5) . ?
O9 S1 1.453(5) . ?
O10 S1 1.461(5) . ?
O11 S2 1.456(5) . ?
O12 S2 1.475(5) . ?
O12 Mn1 2.266(5) 3_646 ?
O13 S2 1.444(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
O1 C1 C2 118.1(6) . . ?
O1 C1 C6 122.3(6) . . ?
C2 C1 C6 119.7(6) . . ?
C3 C2 C1 119.2(7) . . ?
C2 C3 C4 122.0(7) . . ?
C5 C4 C3 118.3(6) . . ?
C5 C4 S1 120.4(5) . . ?
C3 C4 S1 121.3(5) . . ?
C4 C5 C6 121.9(6) . . ?
C5 C6 C1 118.9(6) . . ?
C5 C6 C7 118.3(6) . . ?
C1 C6 C7 122.6(6) . . ?
N1 C7 C6 126.4(6) . . ?
N1 C8 C9 112.4(6) . . ?
C10 C9 C8 115.4(6) . . ?
O2 C10 C9 108.8(5) . . ?
O2 C10 C11 110.0(5) . . ?
C9 C10 C11 111.5(6) . . ?
C10 C11 C12 114.4(6) . . ?
N2 C12 C11 111.9(5) . . ?
N2 C13 C14 125.1(6) . . ?
C15 C14 C19 119.6(6) . . ?
C15 C14 C13 118.3(6) . . ?
C19 C14 C13 122.0(6) . . ?
C16 C15 C14 120.1(7) . . ?
C15 C16 C17 120.7(6) . . ?
C15 C16 S2 121.6(6) . . ?
C17 C16 S2 117.7(5) . . ?
C18 C17 C16 120.1(7) . . ?
C17 C18 C19 120.4(7) . . ?
O3 C19 C18 119.0(6) . . ?
O3 C19 C14 122.0(6) . . ?
C18 C19 C14 119.0(6) . . ?
O1 Mn1 O4 93.5(2) . . ?
O1 Mn1 O2 172.5(2) . . ?
O4 Mn1 O2 79.26(19) . . ?
O1 Mn1 N1 92.9(2) . . ?
O4 Mn1 N1 172.0(2) . . ?
O2 Mn1 N1 94.1(2) . . ?
O1 Mn1 O12 95.8(2) . 3_656 ?
O4 Mn1 O12 93.9(2) . 3_656 ?
O2 Mn1 O12 86.56(19) . 3_656 ?
N1 Mn1 O12 90.1(2) . 3_656 ?
O1 Mn1 O7 89.2(2) . . ?
O4 Mn1 O7 85.8(2) . . ?
O2 Mn1 O7 88.5(2) . . ?
N1 Mn1 O7 89.6(2) . . ?
O12 Mn1 O7 175.01(18) 3_656 . ?
O1 Mn1 Mn2 132.90(15) . . ?
O4 Mn1 Mn2 39.42(14) . . ?
O2 Mn1 Mn2 39.89(13) . . ?
N1 Mn1 Mn2 134.00(17) . . ?
O12 Mn1 Mn2 88.77(12) 3_656 . ?
O7 Mn1 Mn2 87.85(13) . . ?
O3 Mn2 O4 95.2(2) . . ?
O3 Mn2 O2 173.5(2) . . ?
O4 Mn2 O2 79.4(2) . . ?
O3 Mn2 N2 90.8(2) . . ?
O4 Mn2 N2 173.2(2) . . ?
O2 Mn2 N2 94.4(2) . . ?
O3 Mn2 O6 93.8(2) . . ?
O4 Mn2 O6 88.2(2) . . ?
O2 Mn2 O6 89.8(2) . . ?
N2 Mn2 O6 94.5(2) . . ?
O3 Mn2 O5 90.4(2) . . ?
O4 Mn2 O5 87.49(19) . . ?
O2 Mn2 O5 85.73(19) . . ?
N2 Mn2 O5 89.3(2) . . ?
O6 Mn2 O5 174.28(19) . . ?
O3 Mn2 Mn1 134.71(15) . . ?
O4 Mn2 Mn1 39.48(14) . . ?
O2 Mn2 Mn1 39.93(14) . . ?
N2 Mn2 Mn1 134.33(16) . . ?
O6 Mn2 Mn1 87.11(14) . . ?
O5 Mn2 Mn1 87.18(12) . . ?
C7 N1 C8 117.2(6) . . ?
C7 N1 Mn1 122.0(5) . . ?
C8 N1 Mn1 120.8(4) . . ?
C13 N2 C12 118.0(6) . . ?
C13 N2 Mn2 122.3(5) . . ?
C12 N2 Mn2 119.5(4) . . ?
C1 O1 Mn1 126.2(4) . . ?
C10 O2 Mn2 127.9(4) . . ?
C10 O2 Mn1 127.7(4) . . ?
Mn2 O2 Mn1 100.2(2) . . ?
C19 O3 Mn2 122.6(4) . . ?
C20a O4 Mn2 124.3(10) . . ?
C20b O4 Mn2 129(3) . . ?
C20a O4 Mn1 129.6(10) . . ?
C20b O4 Mn1 128(2) . . ?
Mn2 O4 Mn1 101.1(2) . . ?
S2 O12 Mn1 134.1(3) . 3_646 ?
O8 S1 O9 113.1(4) . . ?
O8 S1 O10 111.1(3) . . ?
O9 S1 O10 113.0(3) . . ?
O8 S1 C4 106.6(3) . . ?
O9 S1 C4 105.5(3) . . ?
O10 S1 C4 107.1(3) . . ?
O13 S2 O11 113.4(3) . . ?
O13 S2 O12 110.3(3) . . ?
O11 S2 O12 111.2(3) . . ?
O13 S2 C16 108.1(3) . . ?
O11 S2 C16 107.4(3) . . ?
O12 S2 C16 106.0(3) . . ?

_database_code_depnum_ccdc_archive 'CCDC 1008329'
