# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1552498'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 Mn O6'
_chemical_formula_sum            'C16 H18 Mn O6'
_chemical_formula_weight         361.24

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'
Mn Mn 0.3368 0.7283 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   16.057(2)
_cell_length_b                   6.8909(9)
_cell_length_c                   7.2259(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.608(5)
_cell_angle_gamma                90
_cell_volume                     796.94(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    32.21
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      24.65

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             374
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.856
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'high brillance Incoatec microfocus source'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi end omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7103
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.545
_diffrn_reflns_theta_max         24.714
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.944
_reflns_number_total             1361
_reflns_number_gt                1084
_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 Apex2'
_computing_cell_refinement       'Bruker Saint'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP
_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)+(0.0544P)²+0.9851P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1361
_refine_ls_number_parameters     143
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.049
_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 0.5000 0.0000 0.5000 0.0192(2) Uani 1 2 d S U P . .
O1 O 0.55968(14) 0.4195(3) 0.7515(3) 0.0203(5) Uani 1 1 d . U . . .
O2 O 0.43776(14) 0.2806(3) 0.5052(3) 0.0223(5) Uani 1 1 d . U . . .
H2A H 0.435(3) 0.351(6) 0.410(6) 0.043(12) Uiso 1 1 d . . . . .
H2B H 0.474(3) 0.350(7) 0.586(7) 0.065 Uiso 1 1 d . U . . .
O3 O 0.60204(13) 0.1238(3) 0.6776(3) 0.0239(5) Uani 1 1 d . U . . .
C1 C 0.61741(19) 0.2920(5) 0.7363(4) 0.0188(7) Uani 1 1 d . U . . .
C2B C 0.713(3) 0.312(5) 0.792(9) 0.0221(11) Uani 0.140(8) 1 d D U P A 2
C3B C 0.769(2) 0.159(6) 0.791(8) 0.0281(12) Uani 0.140(8) 1 d D U P A 2
H3B H 0.7486 0.0329 0.7595 0.034 Uiso 0.140(8) 1 calc R U P A 2
C4B C 0.738(2) 0.503(6) 0.820(8) 0.0294(12) Uani 0.140(8) 1 d D U P A 2
H4B H 0.6989 0.6073 0.8072 0.035 Uiso 0.140(8) 1 calc R U P A 2
C5B C 0.8535(19) 0.189(5) 0.836(5) 0.0324(11) Uani 0.140(8) 1 d D U P A 2
H5B H 0.8928 0.0856 0.8488 0.039 Uiso 0.140(8) 1 calc R U P A 2
C6B C 0.875(2) 0.379(5) 0.859(6) 0.0371(12) Uani 0.140(8) 1 d D U P A 2
H6B H 0.9336 0.4069 0.8698 0.045 Uiso 0.140(8) 1 calc R U P A 2
C7B C 0.823(2) 0.535(4) 0.868(6) 0.0364(12) Uani 0.140(8) 1 d D U P A 2
C0AA C 0.855(2) 0.738(4) 0.895(7) 0.077(13) Uani 0.140(8) 1 d D U P A 2
H0AA H 0.8459 0.8100 0.7779 0.115 Uiso 0.140(8) 1 calc R U P A 2
H0AB H 0.9151 0.7347 0.9330 0.115 Uiso 0.140(8) 1 calc R U P A 2
H0AC H 0.8255 0.8028 0.9910 0.115 Uiso 0.140(8) 1 calc R U P A 2
C7A C 0.8046(3) 0.6064(8) 0.8728(8) 0.0364(12) Uani 0.860(8) 1 d D U P A 1
H7A H 0.8172 0.7386 0.8995 0.044 Uiso 0.860(8) 1 calc R U P A 1
C6A C 0.8678(3) 0.4716(9) 0.8737(7) 0.0371(12) Uani 0.860(8) 1 d D U P A 1
H6A H 0.9239 0.5123 0.9024 0.045 Uiso 0.860(8) 1 calc R U P A 1
C5A C 0.8517(3) 0.2778(10) 0.8337(7) 0.0324(11) Uani 0.860(8) 1 d D U P A 1
C3A C 0.7688(3) 0.2223(8) 0.7875(10) 0.0281(12) Uani 0.860(8) 1 d D U P A 1
H3A H 0.7565 0.0908 0.7568 0.034 Uiso 0.860(8) 1 calc R U P A 1
C4A C 0.7226(3) 0.5490(8) 0.8331(10) 0.0294(12) Uani 0.860(8) 1 d D U P A 1
H4A H 0.6786 0.6406 0.8379 0.035 Uiso 0.860(8) 1 calc R U P A 1
C2A C 0.7046(4) 0.3560(8) 0.7858(13) 0.0221(11) Uani 0.860(8) 1 d D U P A 1
C8 C 0.9211(3) 0.1271(8) 0.8481(7) 0.0464(14) Uani 0.860(8) 1 d D U P A 1
H8A H 0.9736 0.1876 0.8182 0.070 Uiso 0.860(8) 1 calc R U P A 1
H8B H 0.9069 0.0213 0.7607 0.070 Uiso 0.860(8) 1 calc R U P A 1
H8C H 0.9275 0.0754 0.9748 0.070 Uiso 0.860(8) 1 calc R U P A 1


_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 2.173(2) 3_656 ?
Mn1 O3 2.173(2) . ?
Mn1 O1 2.174(2) 4_565 ?
Mn1 O1 2.174(2) 2_646 ?
Mn1 O2 2.178(2) 3_656 ?
Mn1 O2 2.178(2) . ?
O1 C1 1.288(4) . ?
O1 Mn1 2.174(2) 2_656 ?
O3 C1 1.252(4) . ?
C1 C2A 1.483(7) . ?
C1 C2B 1.56(5) . ?
C2B C3B 1.380(17) . ?
C2B C4B 1.386(17) . ?
C3B C5B 1.39(2) . ?
C4B C7B 1.40(2) . ?
C5B C6B 1.37(2) . ?
C6B C7B 1.37(2) . ?
C7B C0AA 1.50(2) . ?
C7A C6A 1.376(7) . ?
C7A C4A 1.382(6) . ?
C6A C5A 1.386(8) . ?
C5A C3A 1.399(7) . ?
C5A C8 1.521(7) . ?
C3A C2A 1.382(6) . ?
C4A C2A 1.398(6) . ?

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 180.0 3_656 . ?
O3 Mn1 O1 88.51(8) 3_656 4_565 ?
O3 Mn1 O1 91.49(8) . 4_565 ?
O3 Mn1 O1 91.49(8) 3_656 2_646 ?
O3 Mn1 O1 88.51(8) . 2_646 ?
O1 Mn1 O1 180.00(10) 4_565 2_646 ?
O3 Mn1 O2 88.08(9) 3_656 3_656 ?
O3 Mn1 O2 91.92(9) . 3_656 ?
O1 Mn1 O2 88.79(9) 4_565 3_656 ?
O1 Mn1 O2 91.21(9) 2_646 3_656 ?
O3 Mn1 O2 91.92(9) 3_656 . ?
O3 Mn1 O2 88.08(9) . . ?
O1 Mn1 O2 91.21(9) 4_565 . ?
O1 Mn1 O2 88.79(9) 2_646 . ?
O2 Mn1 O2 180.0 3_656 . ?
C1 O1 Mn1 127.77(18) . 2_656 ?
C1 O3 Mn1 133.0(2) . . ?
O3 C1 O1 122.4(3) . . ?
O3 C1 C2A 120.9(3) . . ?
O1 C1 C2A 116.6(3) . . ?
O3 C1 C2B 109.4(14) . . ?
O1 C1 C2B 128.1(14) . . ?
C3B C2B C4B 123(4) . . ?
C3B C2B C1 124(3) . . ?
C4B C2B C1 113(3) . . ?
C2B C3B C5B 121(4) . . ?
C2B C4B C7B 117(3) . . ?
C6B C5B C3B 114(3) . . ?
C5B C6B C7B 127(3) . . ?
C6B C7B C4B 117(3) . . ?
C6B C7B C0AA 122(3) . . ?
C4B C7B C0AA 120(3) . . ?
C6A C7A C4A 119.9(4) . . ?
C7A C6A C5A 121.6(4) . . ?
C6A C5A C3A 118.1(4) . . ?
C6A C5A C8 121.4(5) . . ?
C3A C5A C8 120.5(5) . . ?
C2A C3A C5A 121.0(5) . . ?
C7A C4A C2A 119.8(5) . . ?
C3A C2A C4A 119.5(5) . . ?
C3A C2A C1 119.6(5) . . ?
C4A C2A C1 120.9(4) . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.080

_shelxl_version_number           2012-9

