# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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 1864041'
_audit_update_record             
;
2018-08-27 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        'C15 H21 Co Na O6'
_chemical_name_common            'C15 H21 Co Na O6'
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C15 H21 Co Na O6'
_chemical_formula_sum            'C15 H21 Co Na O6'
_chemical_formula_weight         379.24

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   16.321(6)
_cell_length_b                   16.321(6)
_cell_length_c                   11.887(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2742(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      4.9
_cell_measurement_theta_max      58.7

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             1182
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    7.818
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.429
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  'Rigaku Saturn 944+'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 22.2222
_diffrn_reflns_number            456
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.9
_diffrn_reflns_theta_max         58.7
_diffrn_reflns_theta_full        58.7
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             412
_reflns_number_gt                412
_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-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.3000P)²] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.011(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         412
_refine_ls_number_parameters     41
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.1043
_refine_ls_wR_factor_ref         0.3295
_refine_ls_wR_factor_gt          0.3295
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.159
_refine_ls_shift/su_mean         0.091

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
Na1 Na 0.666667 0.333333 0.333333 0.119(18) Uani 1 6 d S T P . .
Co1 Co 0.666667 0.333333 0.083333 0.102(7) Uani 1 6 d S T P . .
O1 O 0.6230(9) 0.2144(14) -0.0217(16) 0.076(8) Uani 1 1 d . . . . .
C1 C 0.5953(16) 0.074(2) -0.1019(17) 0.150(15) Uani 1 1 d . . . . .
H1A H 0.576024 0.099449 -0.162635 0.225 Uiso 1 1 calc R U . . .
H1B H 0.642827 0.060415 -0.128113 0.225 Uiso 1 1 calc R U . . .
H1C H 0.541724 0.017093 -0.074804 0.225 Uiso 1 1 calc R U . . .
C2 C 0.666667 0.133(2) 0.083333 0.057(17) Uani 1 2 d S T P . .
H2A H 0.697(18) 0.147(17) 0.06(3) 0.068 Uiso 0.5 1 d . U P . .
C3 C 0.639(2) 0.1519(19) 0.0005(18) 0.102(15) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Na1 0.13(2) 0.13(2) 0.09(3) 0.000 0.000 0.065(12)
Co1 0.103(9) 0.103(9) 0.101(13) 0.000 0.000 0.052(4)
O1 0.078(11) 0.081(12) 0.067(14) -0.008(13) 0.001(11) 0.039(7)
C1 0.13(3) 0.12(2) 0.19(3) 0.03(3) 0.00(3) 0.055(18)
C2 0.06(3) 0.06(3) 0.06(3) -0.005(13) -0.01(3) 0.029(17)
C3 0.12(2) 0.09(2) 0.10(2) 0.00(2) -0.02(2) 0.053(14)

_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
Na1 O1 2.42(2) 18_654 ?
Na1 O1 2.42(2) 22_666 ?
Na1 O1 2.42(2) 17_554 ?
Na1 O1 2.42(2) 16_544 ?
Na1 O1 2.42(2) 23_656 ?
Na1 O1 2.42(2) 24_556 ?
Na1 Co1 2.972(3) . ?
Na1 Co1 2.972(3) 31_655 ?
Co1 O1 2.11(2) 2_655 ?
Co1 O1 2.11(2) . ?
Co1 O1 2.11(2) 18_654 ?
Co1 O1 2.11(2) 17_554 ?
Co1 O1 2.11(2) 16_544 ?
Co1 O1 2.11(2) 3_665 ?
O1 C3 1.20(4) . ?
C1 C3 1.64(3) . ?
C2 C3 1.18(3) . ?
C2 C3 1.18(3) 18_654 ?

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 Na1 O1 105.1(7) 18_654 22_666 ?
O1 Na1 O1 74.9(7) 18_654 17_554 ?
O1 Na1 O1 105.1(7) 22_666 17_554 ?
O1 Na1 O1 74.9(7) 18_654 16_544 ?
O1 Na1 O1 180.0 22_666 16_544 ?
O1 Na1 O1 74.9(7) 17_554 16_544 ?
O1 Na1 O1 105.1(7) 18_654 23_656 ?
O1 Na1 O1 74.9(7) 22_666 23_656 ?
O1 Na1 O1 180.0 17_554 23_656 ?
O1 Na1 O1 105.1(7) 16_544 23_656 ?
O1 Na1 O1 180.0 18_654 24_556 ?
O1 Na1 O1 74.9(7) 22_666 24_556 ?
O1 Na1 O1 105.1(7) 17_554 24_556 ?
O1 Na1 O1 105.1(7) 16_544 24_556 ?
O1 Na1 O1 74.9(7) 23_656 24_556 ?
O1 Na1 Co1 44.6(5) 18_654 . ?
O1 Na1 Co1 135.4(5) 22_666 . ?
O1 Na1 Co1 44.6(5) 17_554 . ?
O1 Na1 Co1 44.6(5) 16_544 . ?
O1 Na1 Co1 135.4(5) 23_656 . ?
O1 Na1 Co1 135.4(5) 24_556 . ?
O1 Na1 Co1 135.4(5) 18_654 31_655 ?
O1 Na1 Co1 44.6(5) 22_666 31_655 ?
O1 Na1 Co1 135.4(5) 17_554 31_655 ?
O1 Na1 Co1 135.4(5) 16_544 31_655 ?
O1 Na1 Co1 44.6(5) 23_656 31_655 ?
O1 Na1 Co1 44.6(5) 24_556 31_655 ?
Co1 Na1 Co1 180.0 . 31_655 ?
O1 Co1 O1 88.6(8) 2_655 . ?
O1 Co1 O1 102.1(8) 2_655 18_654 ?
O1 Co1 O1 82.6(11) . 18_654 ?
O1 Co1 O1 82.6(11) 2_655 17_554 ?
O1 Co1 O1 165.9(9) . 17_554 ?
O1 Co1 O1 88.6(8) 18_654 17_554 ?
O1 Co1 O1 165.9(9) 2_655 16_544 ?
O1 Co1 O1 102.1(8) . 16_544 ?
O1 Co1 O1 88.6(8) 18_654 16_544 ?
O1 Co1 O1 88.6(8) 17_554 16_544 ?
O1 Co1 O1 88.6(8) 2_655 3_665 ?
O1 Co1 O1 88.6(8) . 3_665 ?
O1 Co1 O1 165.9(9) 18_654 3_665 ?
O1 Co1 O1 102.1(8) 17_554 3_665 ?
O1 Co1 O1 82.6(11) 16_544 3_665 ?
O1 Co1 Na1 53.7(5) 2_655 16_544 ?
O1 Co1 Na1 53.7(5) . 16_544 ?
O1 Co1 Na1 126.3(5) 18_654 16_544 ?
O1 Co1 Na1 126.3(5) 17_554 16_544 ?
O1 Co1 Na1 126.3(5) 16_544 16_544 ?
O1 Co1 Na1 53.7(5) 3_665 16_544 ?
O1 Co1 Na1 126.3(5) 2_655 . ?
O1 Co1 Na1 126.3(5) . . ?
O1 Co1 Na1 53.7(5) 18_654 . ?
O1 Co1 Na1 53.7(5) 17_554 . ?
O1 Co1 Na1 53.7(5) 16_544 . ?
O1 Co1 Na1 126.3(5) 3_665 . ?
Na1 Co1 Na1 180.0 16_544 . ?
C3 O1 Co1 122.3(17) . . ?
C3 O1 Na1 137.4(17) . 16_544 ?
Co1 O1 Na1 81.7(7) . 16_544 ?
C3 C2 C3 127(5) . 18_654 ?
C2 C3 O1 132(3) . . ?
C2 C3 C1 119(3) . . ?
O1 C3 C1 107(2) . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.097

