# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_SNNU-74
_database_code_depnum_ccdc_archive 'CCDC 1550550'
_audit_update_record             
;
2017-05-17 deposited with the CCDC.
2019-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 Co Li2 N2 O11'
_chemical_formula_weight         567.26

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'
N N 0.0061 0.0033 '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'

_symmetry_cell_setting           Hexagonal
_symmetry_space_group_name_H-M   R-3

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'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'
'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'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-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'
'-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'

_cell_length_a                   24.8256(4)
_cell_length_b                   24.8256(4)
_cell_length_c                   26.7247(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     14264.0(6)
_cell_formula_units_Z            18
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7425
_cell_measurement_theta_min      3.9440
_cell_measurement_theta_max      28.9620

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             5274
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17394
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5572
_reflns_number_gt                4588
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0924P)²+8.4695P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5572
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1352
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.421859(14) 0.158972(14) 0.059577(12) 0.02334(14) Uani 1 1 d . . .
Li1 Li 0.4507(2) 0.23912(19) -0.02883(18) 0.0349(10) Uani 1 1 d . . .
Li2 Li 0.5361(2) 0.1079(2) 0.0890(2) 0.0470(12) Uani 1 1 d . . .
C1 C 0.39515(12) -0.03970(12) 0.30126(11) 0.0348(6) Uani 1 1 d . . .
C2 C 0.33722(12) 0.06986(12) 0.26506(10) 0.0335(6) Uani 1 1 d . . .
C3 C 0.43010(13) 0.09021(12) 0.14737(10) 0.0335(6) Uani 1 1 d . . .
C4 C 0.34710(12) 0.02749(12) 0.29146(10) 0.0337(6) Uani 1 1 d . . .
H4A H 0.3295 0.0144 0.3230 0.040 Uiso 1 1 calc R . .
C5 C 0.29753(12) 0.09415(13) 0.28651(11) 0.0350(6) Uani 1 1 d . . .
C6 C 0.40948(12) 0.02416(12) 0.22444(10) 0.0349(6) Uani 1 1 d . . .
H6A H 0.4331 0.0083 0.2106 0.042 Uiso 1 1 calc R . .
C7 C 0.36487(12) 0.09003(12) 0.21859(10) 0.0348(6) Uani 1 1 d . . .
H7A H 0.3591 0.1191 0.2010 0.042 Uiso 1 1 calc R . .
C8 C 0.40087(12) 0.06761(12) 0.19798(10) 0.0331(6) Uani 1 1 d . . .
C9 C 0.38305(12) 0.00448(12) 0.27124(11) 0.0338(6) Uani 1 1 d . . .
C10 C 0.54590(11) 0.22241(11) 0.03662(10) 0.0319(6) Uani 1 1 d . . .
C11 C 0.60856(11) 0.28009(11) 0.03225(10) 0.0290(6) Uani 1 1 d . . .
C12 C 0.61352(11) 0.33846(11) 0.03226(10) 0.0304(6) Uani 1 1 d . . .
H12A H 0.5779 0.3418 0.0323 0.037 Uiso 1 1 calc R . .
C13 C 0.46088(18) 0.0213(2) 0.01236(18) 0.0786(13) Uani 1 1 d . . .
H13A H 0.4705 0.0529 -0.0129 0.094 Uiso 1 1 calc R . .
H13B H 0.4281 0.0193 0.0335 0.094 Uiso 1 1 calc R . .
C14 C 0.56149(18) 0.0382(2) 0.0120(2) 0.0862(15) Uani 1 1 d . . .
H14A H 0.5969 0.0471 0.0329 0.103 Uiso 1 1 calc R . .
H14B H 0.5752 0.0707 -0.0132 0.103 Uiso 1 1 calc R . .
C15 C 0.6424(4) 0.1257(5) 0.1533(3) 0.172(4) Uani 1 1 d . . .
C17 C 0.7164(5) 0.1360(6) 0.2159(3) 0.234(6) Uani 1 1 d . . .
C19 C 0.4339(2) 0.3363(3) -0.1107(2) 0.1062(18) Uani 1 1 d . . .
C20 C 0.6087(3) 0.3962(4) -0.0991(3) 0.144(3) Uani 1 1 d . . .
C21 C 0.5381(4) 0.4418(3) -0.1417(3) 0.148(3) Uani 1 1 d . . .
C22' C 0.4974(5) 0.3440(4) -0.0967(3) 0.0498(18) Uani 0.50 1 d P . .
C22 C 0.5335(6) 0.3496(5) -0.0952(3) 0.066(2) Uani 0.50 1 d P . .
N1 N 0.5496(5) 0.3976(4) -0.1104(4) 0.089(3) Uani 0.50 1 d P . .
N1' N 0.5041(8) 0.3743(7) -0.1154(5) 0.104(4) Uani 0.50 1 d P . .
N2 N 0.6792(4) 0.1385(6) 0.1770(3) 0.232(6) Uani 1 1 d . . .
O1 O 0.41985(11) -0.06703(11) 0.28141(9) 0.0512(6) Uani 1 1 d . . .
O2 O 0.37838(9) -0.04537(9) 0.34682(8) 0.0411(5) Uani 1 1 d . . .
O3 O 0.26942(10) 0.07236(10) 0.32643(8) 0.0478(5) Uani 1 1 d . . .
O4 O 0.29629(9) 0.13683(9) 0.26110(8) 0.0438(5) Uani 1 1 d . . .
O5 O 0.41819(10) 0.12894(10) 0.12690(7) 0.0436(5) Uani 1 1 d . . .
O6 O 0.46286(12) 0.07088(11) 0.12969(9) 0.0585(7) Uani 1 1 d . . .
O7 O 0.49852(7) 0.22945(8) 0.03109(7) 0.0330(4) Uani 1 1 d . . .
O8 O 0.54143(9) 0.17225(8) 0.04680(9) 0.0500(6) Uani 1 1 d . . .
O9 O 0.51439(10) 0.03881(10) 0.04186(9) 0.0540(6) Uani 1 1 d . . .
O10 O 0.61028(18) 0.1272(2) 0.12267(17) 0.1273(15) Uani 1 1 d . . .
O11 O 0.50489(12) 0.30192(12) -0.07448(10) 0.0695(7) Uani 1 1 d . . .
C16 C 0.7095(5) 0.2191(4) 0.1565(4) 0.208(5) Uani 1 1 d . . .
C18 C 0.6057(6) 0.0441(4) 0.1751(6) 0.258(7) 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
Co1 O5 1.9323(19) . ?
Co1 O2 1.9335(18) 8_544 ?
Co1 O4 1.9513(17) 13 ?
Co1 O7 1.9832(17) . ?
Co1 Li1 2.938(4) . ?
Li1 O11 1.906(5) . ?
Li1 O3 1.920(5) 13 ?
Li1 O1 1.950(5) 8_544 ?
Li1 O7 2.078(5) . ?
Li2 O10 1.885(6) . ?
Li2 O8 1.904(6) . ?
Li2 O6 1.914(5) . ?
Li2 O9 1.973(6) . ?
C1 O1 1.238(3) . ?
C1 O2 1.271(3) . ?
C1 C9 1.506(3) . ?
C2 C7 1.386(4) . ?
C2 C4 1.387(4) . ?
C2 C5 1.502(3) . ?
C3 O6 1.227(3) . ?
C3 O5 1.263(3) . ?
C3 C8 1.504(4) . ?
C4 C9 1.387(4) . ?
C5 O3 1.241(3) . ?
C5 O4 1.272(3) . ?
C6 C9 1.383(4) . ?
C6 C8 1.393(4) . ?
C7 C8 1.382(4) . ?
C10 O8 1.224(3) . ?
C10 O7 1.281(3) . ?
C10 C11 1.502(3) . ?
C11 C12 1.382(3) 2_655 ?
C11 C12 1.391(3) . ?
C12 C11 1.382(3) 3_665 ?
C13 O9 1.413(4) . ?
C13 C14 1.447(5) 10_655 ?
C14 O9 1.421(4) . ?
C14 C13 1.447(5) 10_655 ?
C15 N2 1.023(8) . ?
C15 O10 1.156(7) . ?
C15 C18 1.853(14) . ?
C15 C16 2.072(14) . ?
C17 N2 1.413(9) . ?
C19 N1' 1.516(17) . ?
C19 C22' 1.537(13) . ?
C20 N1 1.516(15) . ?
C20 C22 1.635(14) . ?
C21 N1 1.516(14) . ?
C21 N1' 1.614(17) . ?
C22' C22 0.837(10) . ?
C22' N1' 0.846(11) . ?
C22' O11 1.294(12) . ?
C22' N1 1.363(13) . ?
C22 N1 1.126(13) . ?
C22 O11 1.171(10) . ?
C22 N1' 1.283(16) . ?
N1 N1' 0.987(14) . ?
N2 C16 1.834(14) . ?
O1 Li1 1.949(5) 6 ?
O2 Co1 1.9334(18) 6 ?
O3 Li1 1.920(5) 13 ?
O4 Co1 1.9513(17) 13 ?

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 O2 110.81(9) . 8_544 ?
O5 Co1 O4 96.14(8) . 13 ?
O2 Co1 O4 108.90(9) 8_544 13 ?
O5 Co1 O7 122.49(8) . . ?
O2 Co1 O7 113.39(9) 8_544 . ?
O4 Co1 O7 102.36(8) 13 . ?
O5 Co1 Li1 163.49(11) . . ?
O2 Co1 Li1 85.63(11) 8_544 . ?
O4 Co1 Li1 79.17(10) 13 . ?
O7 Co1 Li1 44.95(10) . . ?
O11 Li1 O3 113.1(2) . 13 ?
O11 Li1 O1 119.6(3) . 8_544 ?
O3 Li1 O1 108.0(2) 13 8_544 ?
O11 Li1 O7 112.2(2) . . ?
O3 Li1 O7 99.5(2) 13 . ?
O1 Li1 O7 102.1(2) 8_544 . ?
O11 Li1 Co1 154.5(2) . . ?
O3 Li1 Co1 79.78(16) 13 . ?
O1 Li1 Co1 73.15(14) 8_544 . ?
O7 Li1 Co1 42.41(9) . . ?
O10 Li2 O8 114.8(3) . . ?
O10 Li2 O6 115.0(3) . . ?
O8 Li2 O6 113.0(3) . . ?
O10 Li2 O9 109.4(3) . . ?
O8 Li2 O9 103.1(3) . . ?
O6 Li2 O9 99.5(3) . . ?
O1 C1 O2 125.0(2) . . ?
O1 C1 C9 120.3(3) . . ?
O2 C1 C9 114.7(2) . . ?
C7 C2 C4 119.1(2) . . ?
C7 C2 C5 120.2(2) . . ?
C4 C2 C5 120.7(2) . . ?
O6 C3 O5 125.7(3) . . ?
O6 C3 C8 119.4(2) . . ?
O5 C3 C8 114.9(2) . . ?
C2 C4 C9 120.6(2) . . ?
O3 C5 O4 125.4(2) . . ?
O3 C5 C2 119.5(2) . . ?
O4 C5 C2 115.1(2) . . ?
C9 C6 C8 120.2(2) . . ?
C8 C7 C2 121.0(2) . . ?
C7 C8 C6 119.4(2) . . ?
C7 C8 C3 119.8(2) . . ?
C6 C8 C3 120.9(2) . . ?
C6 C9 C4 119.7(2) . . ?
C6 C9 C1 120.5(2) . . ?
C4 C9 C1 119.8(2) . . ?
O8 C10 O7 122.8(2) . . ?
O8 C10 C11 120.7(2) . . ?
O7 C10 C11 116.4(2) . . ?
C12 C11 C12 120.1(2) 2_655 . ?
C12 C11 C10 119.5(2) 2_655 . ?
C12 C11 C10 120.2(2) . . ?
C11 C12 C11 119.9(2) 3_665 . ?
O9 C13 C14 112.8(3) . 10_655 ?
O9 C14 C13 111.4(3) . 10_655 ?
N2 C15 O10 162.1(15) . . ?
N2 C15 C18 91.1(10) . . ?
O10 C15 C18 106.7(9) . . ?
N2 C15 C16 62.2(10) . . ?
O10 C15 C16 100.1(8) . . ?
C18 C15 C16 153.1(8) . . ?
N1' C19 C22' 32.2(5) . . ?
N1 C20 C22 41.7(5) . . ?
N1 C21 N1' 36.6(5) . . ?
C22 C22' N1' 99.3(18) . . ?
C22 C22' O11 62.4(11) . . ?
N1' C22' O11 160.7(18) . . ?
C22 C22' N1 55.6(11) . . ?
N1' C22' N1 46.1(12) . . ?
O11 C22' N1 117.5(12) . . ?
C22 C22' C19 168.5(13) . . ?
N1' C22' C19 72.6(16) . . ?
O11 C22' C19 124.4(7) . . ?
N1 C22' C19 118.1(13) . . ?
C22' C22 N1 86.7(13) . . ?
C22' C22 O11 78.3(14) . . ?
N1 C22 O11 162.8(16) . . ?
C22' C22 N1' 40.6(11) . . ?
N1 C22 N1' 47.8(7) . . ?
O11 C22 N1' 118.6(17) . . ?
C22' C22 C20 149.8(14) . . ?
N1 C22 C20 63.5(11) . . ?
O11 C22 C20 130.2(10) . . ?
N1' C22 C20 110.9(11) . . ?
N1' N1 C22 74.4(10) . . ?
N1' N1 C22' 38.1(8) . . ?
C22 N1 C22' 37.8(5) . . ?
N1' N1 C21 77.1(16) . . ?
C22 N1 C21 150.4(14) . . ?
C22' N1 C21 115.1(13) . . ?
N1' N1 C20 148.2(16) . . ?
C22 N1 C20 74.9(13) . . ?
C22' N1 C20 112.5(12) . . ?
C21 N1 C20 131.4(7) . . ?
C22' N1' N1 95.8(18) . . ?
C22' N1' C22 40.1(10) . . ?
N1 N1' C22 57.7(11) . . ?
C22' N1' C19 75.2(17) . . ?
N1 N1' C19 167.4(17) . . ?
C22 N1' C19 114.9(15) . . ?
C22' N1' C21 161.5(19) . . ?
N1 N1' C21 66.3(14) . . ?
C22 N1' C21 123.5(15) . . ?
C19 N1' C21 121.5(9) . . ?
C15 N2 C17 160.7(16) . . ?
C15 N2 C16 88.2(10) . . ?
C17 N2 C16 110.4(10) . . ?
C1 O1 Li1 136.0(2) . 6 ?
C1 O2 Co1 119.48(16) . 6 ?
C5 O3 Li1 128.4(2) . 13 ?
C5 O4 Co1 126.85(18) . 13 ?
C3 O5 Co1 135.49(18) . . ?
C3 O6 Li2 133.4(2) . . ?
C10 O7 Co1 112.14(15) . . ?
C10 O7 Li1 136.2(2) . . ?
Co1 O7 Li1 92.64(13) . . ?
C10 O8 Li2 156.6(3) . . ?
C13 O9 C14 109.6(3) . . ?
C13 O9 Li2 115.4(2) . . ?
C14 O9 Li2 119.9(3) . . ?
C15 O10 Li2 158.8(7) . . ?
C22 O11 C22' 39.3(6) . . ?
C22 O11 Li1 162.3(6) . . ?
C22' O11 Li1 128.8(5) . . ?
N2 C16 C15 29.6(3) . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 971 83 ' '
2 0.000 0.000 0.500 14 0 ' '
3 0.333 0.667 0.667 968 83 ' '
4 0.333 0.667 0.167 15 0 ' '
5 0.667 0.333 0.333 968 83 ' '
6 0.667 0.333 0.833 15 0 ' '
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.069
