# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_1a_a
_database_code_depnum_ccdc_archive 'CCDC 1504126'
_audit_update_record             
;
2016-12-01 deposited with the CCDC.
2016-12-16 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            'C8 H20 Co O9'
_chemical_formula_weight         319.17

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'
Co Co 0.3494 0.9721 '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                   9.8852(5)
_cell_length_b                   16.8825(9)
_cell_length_c                   8.1720(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.423(2)
_cell_angle_gamma                90
_cell_volume                     1361.37(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_F_000             668
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.295
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.6467
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Sheldrick,1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19349
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_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             2376
_reflns_number_gt                1915
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0947P)²+11.0356P] 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         2376
_refine_ls_number_parameters     205
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1984
_refine_ls_wR_factor_gt          0.1911
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.055
_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
Co1 Co 0.72031(8) 0.74864(5) 0.53045(9) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.4876(6) 0.8654(4) 0.5157(7) 0.0208(12) Uani 1 1 d . . . . .
O1 O 0.5710(4) 0.8235(3) 0.4386(5) 0.0295(10) Uani 1 1 d . . . . .
O2 O 0.4951(5) 0.8747(3) 0.6650(5) 0.0352(12) Uani 1 1 d . . . . .
C2 C 0.3768(6) 0.9042(4) 0.4050(8) 0.0277(14) Uani 1 1 d . . . . .
H2 H 0.423901 0.931473 0.319119 0.033 Uiso 1 1 calc R U . . .
O3 O -0.1288(4) 0.8218(3) 0.4573(5) 0.0299(11) Uani 1 1 d . . . . .
C3 C 0.2839(7) 0.8428(5) 0.3157(8) 0.0348(16) Uani 1 1 d . . . . .
H3A H 0.244559 0.866288 0.215458 0.042 Uiso 1 1 calc R U . . .
H3B H 0.338211 0.797888 0.285446 0.042 Uiso 1 1 calc R U . . .
O6 O 0.7181(4) 0.6980(3) 0.2844(5) 0.0212(9) Uani 1 1 d D . . . .
H6D H 0.656(5) 0.667(3) 0.248(8) 0.025 Uiso 1 1 d D U . . .
H6C H 0.793(4) 0.675(4) 0.272(8) 0.025 Uiso 1 1 d D U . . .
C6 C 0.1779(6) 0.9379(4) 0.5824(9) 0.0316(15) Uani 1 1 d . . . . .
H6A H 0.125637 0.982514 0.618609 0.038 Uiso 1 1 calc R U . . .
H6B H 0.212683 0.909123 0.678692 0.038 Uiso 1 1 calc R U . . .
O5 O 0.5794(6) 0.6723(3) 0.6116(6) 0.0439(14) Uani 1 1 d D . . . .
H5D H 0.507(5) 0.654(5) 0.564(10) 0.053 Uiso 1 1 d D U . . .
H5C H 0.562(9) 0.674(5) 0.712(4) 0.053 Uiso 1 1 d D U . . .
C5 C 0.1695(6) 0.8133(4) 0.4184(9) 0.0314(15) Uani 1 1 d . . . . .
H5A H 0.111165 0.777647 0.353408 0.038 Uiso 1 1 calc R U . . .
H5B H 0.207460 0.784424 0.512844 0.038 Uiso 1 1 calc R U . . .
O4 O -0.0534(5) 0.8659(3) 0.7007(5) 0.0419(14) Uani 1 1 d . . . . .
C4 C 0.2955(6) 0.9678(4) 0.4875(9) 0.0341(16) Uani 1 1 d . . . . .
H4A H 0.356560 0.997276 0.562181 0.041 Uiso 1 1 calc R U . . .
H4B H 0.260150 1.004369 0.404016 0.041 Uiso 1 1 calc R U . . .
C8 C -0.0400(6) 0.8561(4) 0.5532(8) 0.0256(14) Uani 1 1 d . . . . .
O7 O 0.8676(6) 0.6713(4) 0.6280(6) 0.0448(14) Uani 1 1 d D . . . .
H7C H 0.952(3) 0.667(5) 0.619(9) 0.054 Uiso 1 1 d D U . . .
H7D H 0.858(7) 0.667(5) 0.730(3) 0.054 Uiso 1 1 d D U . . .
C7 C 0.0866(6) 0.8836(4) 0.4754(8) 0.0267(14) Uani 1 1 d . . . . .
H7 H 0.057260 0.913881 0.377231 0.032 Uiso 1 1 calc R U . . .
O8A O 1.0919(13) 0.5991(10) 0.4791(13) 0.041(5) Uani 0.51(3) 1 d D . P A 1
H8B H 1.086(12) 0.5486(16) 0.479(12) 0.049 Uiso 1 1 d D U . B 1
H8A H 1.047(8) 0.592(5) 0.388(6) 0.049 Uiso 1 1 d D U . C 1
O8B O 1.003(2) 0.5573(10) 0.4848(15) 0.063(8) Uani 0.49(3) 1 d . . P A 2
O9B O 0.6218(11) 0.4113(6) 0.5515(13) 0.027(2) Uiso 0.4 1 d . . P D 1
O9C O 0.7551(14) 0.5220(8) 0.4712(18) 0.025(3) Uani 0.3 1 d . . P E 2
O9A O 0.5164(15) 0.4553(8) 0.5459(17) 0.027(3) Uiso 0.3 1 d . . P F 3


_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
Co1 O5 2.038(5) . ?
Co1 O1 2.052(4) . ?
Co1 O3 2.053(4) 1_655 ?
Co1 O7 2.078(5) . ?
Co1 O6 2.184(4) . ?
Co1 O6 2.264(4) 4_576 ?
C1 O2 1.228(7) . ?
C1 O1 1.280(7) . ?
C1 C2 1.526(9) . ?
C2 C4 1.522(9) . ?
C2 C3 1.540(9) . ?
C2 H2 0.9800 . ?
O3 C8 1.279(8) . ?
C3 C5 1.531(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O6 H6D 0.85(2) . ?
O6 H6C 0.85(2) . ?
C6 C4 1.522(9) . ?
C6 C7 1.524(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O5 H5D 0.85(2) . ?
O5 H5C 0.85(2) . ?
C5 C7 1.530(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
O4 C8 1.232(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C8 C7 1.511(8) . ?
O7 H7C 0.85(2) . ?
O7 H7D 0.85(2) . ?
C7 H7 0.9800 . ?
O8A H8B 0.85(2) . ?
O8A H8A 0.85(2) . ?
O9A O9A 1.71(3) 3_666 ?

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
O5 Co1 O1 91.0(2) . . ?
O5 Co1 O3 176.5(2) . 1_655 ?
O1 Co1 O3 92.40(19) . 1_655 ?
O5 Co1 O7 87.4(3) . . ?
O1 Co1 O7 178.3(2) . . ?
O3 Co1 O7 89.2(2) 1_655 . ?
O5 Co1 O6 94.72(18) . . ?
O1 Co1 O6 86.41(16) . . ?
O3 Co1 O6 86.27(16) 1_655 . ?
O7 Co1 O6 94.33(18) . . ?
O5 Co1 O6 84.82(17) . 4_576 ?
O1 Co1 O6 92.51(16) . 4_576 ?
O3 Co1 O6 94.25(16) 1_655 4_576 ?
O7 Co1 O6 86.74(18) . 4_576 ?
O6 Co1 O6 178.8(2) . 4_576 ?
O2 C1 O1 123.9(6) . . ?
O2 C1 C2 122.2(5) . . ?
O1 C1 C2 113.9(5) . . ?
C1 O1 Co1 129.1(4) . . ?
C4 C2 C1 114.8(5) . . ?
C4 C2 C3 111.6(5) . . ?
C1 C2 C3 112.3(6) . . ?
C4 C2 H2 105.8 . . ?
C1 C2 H2 105.8 . . ?
C3 C2 H2 105.8 . . ?
C8 O3 Co1 125.3(4) . 1_455 ?
C5 C3 C2 113.5(5) . . ?
C5 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C5 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
Co1 O6 Co1 133.5(2) . 4_575 ?
Co1 O6 H6D 122(5) . . ?
Co1 O6 H6D 89(5) 4_575 . ?
Co1 O6 H6C 109(5) . . ?
Co1 O6 H6C 91(5) 4_575 . ?
H6D O6 H6C 107(7) . . ?
C4 C6 C7 110.6(6) . . ?
C4 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
Co1 O5 H5D 131(6) . . ?
Co1 O5 H5C 118(6) . . ?
H5D O5 H5C 104(8) . . ?
C7 C5 C3 110.0(6) . . ?
C7 C5 H5A 109.7 . . ?
C3 C5 H5A 109.7 . . ?
C7 C5 H5B 109.7 . . ?
C3 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C6 C4 C2 115.6(6) . . ?
C6 C4 H4A 108.4 . . ?
C2 C4 H4A 108.4 . . ?
C6 C4 H4B 108.4 . . ?
C2 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
O4 C8 O3 123.4(6) . . ?
O4 C8 C7 120.7(6) . . ?
O3 C8 C7 115.9(5) . . ?
Co1 O7 H7C 133(6) . . ?
Co1 O7 H7D 108(5) . . ?
H7C O7 H7D 105(3) . . ?
C8 C7 C6 114.9(5) . . ?
C8 C7 C5 111.2(5) . . ?
C6 C7 C5 109.3(5) . . ?
C8 C7 H7 107.0 . . ?
C6 C7 H7 107.0 . . ?
C5 C7 H7 107.0 . . ?
H8B O8A H8A 79(9) . . ?

_refine_diff_density_max         1.244
_refine_diff_density_min         -1.104
_refine_diff_density_rms         0.130

