# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1586491'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-01-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Li2 Mn O10'
_chemical_formula_weight         433.08

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'
Li Li -0.0003 0.0001 '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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   16.390(6)
_cell_length_b                   10.753(4)
_cell_length_c                   10.349(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.528(5)
_cell_angle_gamma                90
_cell_volume                     1696.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2630
_cell_measurement_theta_min      2.1154
_cell_measurement_theta_max      27.4778

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1800
_exptl_crystal_size_mid          0.0800
_exptl_crystal_size_min          0.0400
_exptl_absorpt_coefficient_mu    0.835
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9142
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6364
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.788
_diffrn_reflns_theta_max         25.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1651
_reflns_number_gt                1503
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND. Version 3.2. Crystal Impact'
_computing_publication_material  'Windows Word 2010'
_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)+(0.0421P)²+2.1399P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1651
_refine_ls_number_parameters     126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0866
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
Mn1 Mn 0.500000 -0.08878(4) -0.250000 0.02239(15) Uani 1 2 d S T P . .
O1 O 0.39545(8) -0.01135(13) -0.43916(13) 0.02239(15) Uani 1 1 d . . . . .
O2 O 0.39470(9) 0.06467(14) -0.24352(14) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.01368(9) 0.30047(15) -0.42157(17) 0.0331(4) Uani 1 1 d . . . . .
O4 O 0.12870(11) 0.27513(17) -0.23151(16) 0.0399(4) Uani 1 1 d . . . . .
O5 O 0.33003(13) 0.27681(19) -0.06188(18) 0.0531(5) Uani 1 1 d . . . . .
H5B H 0.274323 0.279829 -0.093857 0.064 Uiso 1 1 d R U . . .
H5A H 0.337464 0.281849 0.023673 0.064 Uiso 1 1 d R U . . .
C1 C 0.35671(13) 0.04512(18) -0.3713(2) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.08935(13) 0.2566(2) -0.3580(2) 0.0260(5) Uani 1 1 d . . . . .
C3 C 0.26335(13) 0.08336(18) -0.4443(2) 0.0212(4) Uani 1 1 d . . . . .
C4 C 0.21967(12) 0.14688(18) -0.3725(2) 0.0220(4) Uani 1 1 d . . . . .
H4A H 0.249027 0.165921 -0.279229 0.026 Uiso 1 1 calc R U . . .
C5 C 0.13273(12) 0.18247(19) -0.4379(2) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.08891(14) 0.1522(2) -0.5766(2) 0.0345(5) Uani 1 1 d . . . . .
H6A H 0.030525 0.175008 -0.621246 0.041 Uiso 1 1 calc R U . . .
C7 C 0.13222(16) 0.0877(3) -0.6488(2) 0.0428(7) Uani 1 1 d . . . . .
H7A H 0.102535 0.066796 -0.741504 0.051 Uiso 1 1 calc R U . . .
C8 C 0.21924(15) 0.0547(2) -0.5834(2) 0.0325(5) Uani 1 1 d . . . . .
H8A H 0.248305 0.013213 -0.632748 0.039 Uiso 1 1 calc R U . . .
Li1 Li 0.4074(2) 0.1376(4) -0.0675(4) 0.0290(8) 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 O3 2.2167(17) 3_545 ?
Mn1 O3 2.2167(17) 4_544 ?
Mn1 O1 2.2361(14) 2_654 ?
Mn1 O1 2.2361(14) . ?
Mn1 O2 2.4064(15) 2_654 ?
Mn1 O2 2.4064(15) . ?
Mn1 O4 2.5163(17) 4_544 ?
Mn1 O4 2.5163(17) 3_545 ?
Mn1 Li1 3.117(4) 6 ?
Mn1 Li1 3.117(4) 5_655 ?
O1 C1 1.262(2) . ?
O1 Li1 1.959(4) 6 ?
O2 C1 1.256(2) . ?
O2 Li1 1.923(4) . ?
O3 C2 1.263(3) . ?
O3 Li1 1.957(4) 8_455 ?
O4 C2 1.245(3) . ?
O5 Li1 1.977(4) . ?
O5 H5B 0.8500 . ?
O5 H5A 0.8500 . ?
C1 C3 1.494(3) . ?
C2 C5 1.502(3) . ?
C3 C8 1.388(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.388(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.388(3) . ?
C6 C7 1.390(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.382(3) . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9300 . ?
Li1 H5A 2.3250 . ?

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
O3 Mn1 O3 115.01(9) 3_545 4_544 ?
O3 Mn1 O1 129.13(5) 3_545 2_654 ?
O3 Mn1 O1 76.65(6) 4_544 2_654 ?
O3 Mn1 O1 76.65(6) 3_545 . ?
O3 Mn1 O1 129.13(5) 4_544 . ?
O1 Mn1 O1 136.28(8) 2_654 . ?
O3 Mn1 O2 93.53(6) 3_545 2_654 ?
O3 Mn1 O2 132.46(5) 4_544 2_654 ?
O1 Mn1 O2 56.08(5) 2_654 2_654 ?
O1 Mn1 O2 92.71(5) . 2_654 ?
O3 Mn1 O2 132.46(5) 3_545 . ?
O3 Mn1 O2 93.53(6) 4_544 . ?
O1 Mn1 O2 92.71(5) 2_654 . ?
O1 Mn1 O2 56.08(5) . . ?
O2 Mn1 O2 93.42(8) 2_654 . ?
O3 Mn1 O4 87.42(6) 3_545 4_544 ?
O3 Mn1 O4 54.55(5) 4_544 4_544 ?
O1 Mn1 O4 129.41(5) 2_654 4_544 ?
O1 Mn1 O4 78.36(6) . 4_544 ?
O2 Mn1 O4 170.56(5) 2_654 4_544 ?
O2 Mn1 O4 79.11(6) . 4_544 ?
O3 Mn1 O4 54.55(5) 3_545 3_545 ?
O3 Mn1 O4 87.42(6) 4_544 3_545 ?
O1 Mn1 O4 78.36(6) 2_654 3_545 ?
O1 Mn1 O4 129.41(5) . 3_545 ?
O2 Mn1 O4 79.11(6) 2_654 3_545 ?
O2 Mn1 O4 170.56(5) . 3_545 ?
O4 Mn1 O4 108.88(9) 4_544 3_545 ?
O3 Mn1 Li1 38.59(8) 3_545 6 ?
O3 Mn1 Li1 126.93(8) 4_544 6 ?
O1 Mn1 Li1 154.94(8) 2_654 6 ?
O1 Mn1 Li1 38.69(8) . 6 ?
O2 Mn1 Li1 99.37(8) 2_654 6 ?
O2 Mn1 Li1 93.90(8) . 6 ?
O4 Mn1 Li1 75.62(8) 4_544 6 ?
O4 Mn1 Li1 93.01(8) 3_545 6 ?
O3 Mn1 Li1 126.93(8) 3_545 5_655 ?
O3 Mn1 Li1 38.59(8) 4_544 5_655 ?
O1 Mn1 Li1 38.69(8) 2_654 5_655 ?
O1 Mn1 Li1 154.94(8) . 5_655 ?
O2 Mn1 Li1 93.90(8) 2_654 5_655 ?
O2 Mn1 Li1 99.37(8) . 5_655 ?
O4 Mn1 Li1 93.01(8) 4_544 5_655 ?
O4 Mn1 Li1 75.62(8) 3_545 5_655 ?
Li1 Mn1 Li1 160.63(14) 6 5_655 ?
C1 O1 Li1 155.08(17) . 6 ?
C1 O1 Mn1 94.16(12) . . ?
Li1 O1 Mn1 95.77(12) 6 . ?
C1 O2 Li1 154.89(17) . . ?
C1 O2 Mn1 86.52(11) . . ?
Li1 O2 Mn1 118.46(13) . . ?
C2 O3 Li1 162.79(19) . 8_455 ?
C2 O3 Mn1 98.75(14) . 3_455 ?
Li1 O3 Mn1 96.45(13) 8_455 3_455 ?
C2 O4 Mn1 85.22(13) . 3_455 ?
Li1 O5 H5B 128.8 . . ?
Li1 O5 H5A 103.3 . . ?
H5B O5 H5A 97.2 . . ?
O1 C1 O2 120.69(18) . . ?
O1 C1 C3 118.83(17) . . ?
O2 C1 C3 120.42(17) . . ?
O4 C2 O3 121.3(2) . . ?
O4 C2 C5 119.76(18) . . ?
O3 C2 C5 118.98(19) . . ?
C8 C3 C4 119.37(18) . . ?
C8 C3 C1 120.68(18) . . ?
C4 C3 C1 119.94(17) . . ?
C3 C4 C5 120.95(18) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 119.25(19) . . ?
C4 C5 C2 119.12(18) . . ?
C6 C5 C2 121.60(18) . . ?
C7 C6 C5 120.04(19) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C3 C8 C7 120.1(2) . . ?
C3 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
O2 Li1 O1 110.92(19) . 6_556 ?
O2 Li1 O3 128.8(2) . 8_556 ?
O1 Li1 O3 89.69(16) 6_556 8_556 ?
O2 Li1 O5 119.28(19) . . ?
O1 Li1 O5 106.26(18) 6_556 . ?
O3 Li1 O5 96.79(18) 8_556 . ?
O2 Li1 Mn1 140.50(18) . 5_655 ?
O1 Li1 Mn1 45.54(8) 6_556 5_655 ?
O3 Li1 Mn1 44.96(9) 8_556 5_655 ?
O5 Li1 Mn1 99.54(14) . 5_655 ?
O2 Li1 H5A 139.3 . . ?
O1 Li1 H5A 90.0 6_556 . ?
O3 Li1 H5A 83.8 8_556 . ?
O5 Li1 H5A 20.8 . . ?
Mn1 Li1 H5A 78.8 5_655 . ?

_refine_diff_density_max         0.520
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.060


_exptl_crystal_preparation       'Magnetic properties'
