# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_KP-97
_database_code_depnum_ccdc_archive 'CCDC 1573318'
_audit_update_record             
;
2017-09-08 deposited with the CCDC.
2018-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H18 Mn O8'
_chemical_formula_sum            'C10 H18 Mn O8'
_chemical_formula_weight         321.18

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'
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'
H H 0.0000 0.0000 '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                   8.7974(5)
_cell_length_b                   6.6960(4)
_cell_length_c                   23.1544(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.145(5)
_cell_angle_gamma                90
_cell_volume                     1361.91(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    110.8(2)
_cell_measurement_reflns_used    2452
_cell_measurement_theta_min      3.5030
_cell_measurement_theta_max      27.8470

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.000
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.73179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110.8(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         2
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_decay_%        0
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5188
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.989
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2369
_reflns_number_gt                2127
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0484P)²+10.0066P] 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         2369
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1519
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_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
C1 C 0.5429(5) -0.1346(7) 0.3026(2) 0.0114(10) Uani 1 1 d . . . . .
C2 C 0.5576(5) 0.0560(7) 0.3377(2) 0.0113(10) Uani 1 1 d . . . . .
H2A H 0.5782 0.0244 0.3783 0.014 Uiso 1 1 calc R U . . .
H2B H 0.6413 0.1358 0.3247 0.014 Uiso 1 1 calc R U . . .
C3 C 0.4219(6) 0.3594(7) 0.3568(2) 0.0166(11) Uani 1 1 d . . . . .
H3A H 0.3597 0.4511 0.3333 0.020 Uiso 1 1 calc R U . . .
H3B H 0.5255 0.4094 0.3590 0.020 Uiso 1 1 calc R U . . .
C4 C 0.3636(6) 0.3494(9) 0.4164(2) 0.0229(12) Uani 1 1 d . . . . .
H4A H 0.3411 0.4829 0.4298 0.027 Uiso 1 1 calc R U . . .
H4B H 0.2705 0.2717 0.4157 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4224(7) 0.2378(9) 0.5112(3) 0.0302(14) Uani 1 1 d . . . . .
H5A H 0.3982 0.3669 0.5262 0.045 Uiso 1 1 calc R U . . .
H5B H 0.5000 0.1765 0.5360 0.045 Uiso 1 1 calc R U . . .
H5C H 0.3329 0.1555 0.5096 0.045 Uiso 1 1 calc R U . . .
C6 C 0.0229(5) -0.2370(7) 0.1986(2) 0.0114(10) Uani 1 1 d . . . . .
C7 C 0.0295(5) -0.4261(7) 0.1632(2) 0.0110(10) Uani 1 1 d . . . . .
H7A H 0.0491 -0.3934 0.1235 0.013 Uiso 1 1 calc R U . . .
H7B H 0.1116 -0.5107 0.1786 0.013 Uiso 1 1 calc R U . . .
C8 C -0.1045(6) -0.7364(7) 0.1492(2) 0.0143(10) Uani 1 1 d . . . . .
H8A H -0.2037 -0.7963 0.1532 0.017 Uiso 1 1 calc R U . . .
H8B H -0.0329 -0.8035 0.1760 0.017 Uiso 1 1 calc R U . . .
C9 C -0.0571(6) -0.7729(8) 0.0883(2) 0.0189(11) Uani 1 1 d . . . . .
H9A H 0.0421 -0.7139 0.0835 0.023 Uiso 1 1 calc R U . . .
H9B H -0.0497 -0.9154 0.0814 0.023 Uiso 1 1 calc R U . . .
C10 C -0.1353(7) -0.7375(10) -0.0093(2) 0.0313(14) Uani 1 1 d . . . . .
H10A H -0.0373 -0.6863 -0.0181 0.047 Uiso 1 1 calc R U . . .
H10B H -0.2121 -0.6802 -0.0353 0.047 Uiso 1 1 calc R U . . .
H10C H -0.1359 -0.8801 -0.0136 0.047 Uiso 1 1 calc R U . . .
O1 O 0.4199(4) -0.1685(5) 0.27257(15) 0.0141(7) Uani 1 1 d . . . . .
O2 O 0.6589(4) -0.2459(5) 0.30545(15) 0.0149(8) Uani 1 1 d . . . . .
O3 O 0.4181(4) 0.1652(5) 0.33024(15) 0.0134(7) Uani 1 1 d . . . . .
O4 O 0.4755(4) 0.2592(6) 0.45485(16) 0.0236(9) Uani 1 1 d . . . . .
O5 O -0.0931(4) -0.2039(5) 0.22594(14) 0.0131(7) Uani 1 1 d . . . . .
O6 O 0.1392(4) -0.1274(5) 0.19761(15) 0.0149(8) Uani 1 1 d . . . . .
O7 O -0.1119(4) -0.5292(5) 0.16510(15) 0.0125(7) Uani 1 1 d . . . . .
O8 O -0.1655(5) -0.6876(6) 0.04812(16) 0.0260(9) Uani 1 1 d . . . . .
Mn1 Mn 0.25533(8) 0.06407(11) 0.25853(3) 0.0104(2) 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
C1 O2 1.262(6) . ?
C1 O1 1.274(6) . ?
C1 C2 1.515(7) . ?
C2 O3 1.430(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O3 1.438(6) . ?
C3 C4 1.501(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O4 1.424(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O4 1.417(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O5 1.250(6) . ?
C6 O6 1.260(6) . ?
C6 C7 1.512(7) . ?
C7 O7 1.425(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O7 1.438(6) . ?
C8 C9 1.511(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O8 1.416(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O8 1.410(7) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O1 Mn1 2.139(3) . ?
O2 Mn1 2.123(3) 2_645 ?
O3 Mn1 2.237(3) . ?
O5 Mn1 2.153(3) 2_545 ?
O6 Mn1 2.126(3) . ?
O7 Mn1 2.314(3) 2_545 ?
Mn1 O2 2.123(3) 2_655 ?
Mn1 O5 2.153(3) 2 ?
Mn1 O7 2.314(3) 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
O2 C1 O1 125.7(5) . . ?
O2 C1 C2 115.1(4) . . ?
O1 C1 C2 119.2(4) . . ?
O3 C2 C1 108.6(4) . . ?
O3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
O3 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O3 C3 C4 110.6(4) . . ?
O3 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
O4 C4 C3 109.5(4) . . ?
O4 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
O4 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
O4 C5 H5A 109.5 . . ?
O4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O5 C6 O6 126.4(5) . . ?
O5 C6 C7 118.7(4) . . ?
O6 C6 C7 115.0(4) . . ?
O7 C7 C6 109.2(4) . . ?
O7 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
O7 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O7 C8 C9 114.5(4) . . ?
O7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
O7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
O8 C9 C8 109.7(4) . . ?
O8 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O8 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O8 C10 H10A 109.5 . . ?
O8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 O1 Mn1 120.0(3) . . ?
C1 O2 Mn1 129.4(3) . 2_645 ?
C2 O3 C3 114.3(4) . . ?
C2 O3 Mn1 116.4(3) . . ?
C3 O3 Mn1 126.1(3) . . ?
C5 O4 C4 111.5(4) . . ?
C6 O5 Mn1 121.6(3) . 2_545 ?
C6 O6 Mn1 134.4(3) . . ?
C7 O7 C8 114.0(4) . . ?
C7 O7 Mn1 114.0(3) . 2_545 ?
C8 O7 Mn1 119.4(3) . 2_545 ?
C10 O8 C9 111.6(4) . . ?
O2 Mn1 O6 94.29(13) 2_655 . ?
O2 Mn1 O1 106.20(13) 2_655 . ?
O6 Mn1 O1 87.61(14) . . ?
O2 Mn1 O5 87.03(13) 2_655 2 ?
O6 Mn1 O5 104.32(13) . 2 ?
O1 Mn1 O5 161.67(13) . 2 ?
O2 Mn1 O3 95.68(13) 2_655 . ?
O6 Mn1 O3 159.99(13) . . ?
O1 Mn1 O3 72.96(13) . . ?
O5 Mn1 O3 93.50(13) 2 . ?
O2 Mn1 O7 157.62(13) 2_655 2 ?
O6 Mn1 O7 94.70(13) . 2 ?
O1 Mn1 O7 94.61(12) . 2 ?
O5 Mn1 O7 70.90(12) 2 2 ?
O3 Mn1 O7 82.43(12) . 2 ?

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
O2 C1 C2 O3 -179.9(4) . . . . ?
O1 C1 C2 O3 1.3(6) . . . . ?
O3 C3 C4 O4 74.5(5) . . . . ?
O5 C6 C7 O7 4.1(6) . . . . ?
O6 C6 C7 O7 -176.3(4) . . . . ?
O7 C8 C9 O8 -62.2(6) . . . . ?
O2 C1 O1 Mn1 -166.6(4) . . . . ?
C2 C1 O1 Mn1 12.0(6) . . . . ?
O1 C1 O2 Mn1 31.7(7) . . . 2_645 ?
C2 C1 O2 Mn1 -147.0(3) . . . 2_645 ?
C1 C2 O3 C3 -174.2(4) . . . . ?
C1 C2 O3 Mn1 -13.0(5) . . . . ?
C4 C3 O3 C2 -93.7(5) . . . . ?
C4 C3 O3 Mn1 107.3(4) . . . . ?
C3 C4 O4 C5 -177.1(5) . . . . ?
O6 C6 O5 Mn1 -163.8(4) . . . 2_545 ?
C7 C6 O5 Mn1 15.6(6) . . . 2_545 ?
O5 C6 O6 Mn1 33.2(7) . . . . ?
C7 C6 O6 Mn1 -146.3(3) . . . . ?
C6 C7 O7 C8 -161.3(4) . . . . ?
C6 C7 O7 Mn1 -19.5(4) . . . 2_545 ?
C9 C8 O7 C7 -60.9(5) . . . . ?
C9 C8 O7 Mn1 159.5(3) . . . 2_545 ?
C8 C9 O8 C10 -173.2(5) . . . . ?

_refine_diff_density_max         1.412
_refine_diff_density_min         -1.054
_refine_diff_density_rms         0.123

_shelxl_version_number           2013-4

