# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_h06rdk15
_database_code_depnum_ccdc_archive 'CCDC 1562215'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2018-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'hexacarbonyl ?-{η4-[2,4-dimethyl-2-(1-benzyloxyprop-1-yl)-8-oxabicyclo[3.2.1]octan-3-one]}dicobalt(Co-Co)'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 Co2 O9'
_chemical_formula_sum            'C25 H22 Co2 O9'
_chemical_formula_weight         584.29

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   8.57600(10)
_cell_length_b                   9.05900(10)
_cell_length_c                   16.3000(3)
_cell_angle_alpha                81.0490(10)
_cell_angle_beta                 89.2630(10)
_cell_angle_gamma                78.6610(10)
_cell_volume                     1226.30(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    24680
_cell_measurement_theta_min      2.910
_cell_measurement_theta_max      30.034

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5347
_exptl_absorpt_correction_T_max  0.7587
_exptl_absorpt_process_details   
;
 multi-scan from symmetry-related measurements,
 Blessing, R. H.  Acta Cryst., 1995, A51, 33-38.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Nonius Kappa CCD'
_diffrn_measurement_method       '328, 1.8 degree images with ω scans'
_diffrn_standards_number         0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            31059
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.13
_diffrn_reflns_theta_max         30.10
_reflns_number_total             7141
_reflns_number_gt                5778
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinski & Minor, 1997)'
_computing_data_reduction        
;
 DENZO-SCALEPACK Z. Otwinowski and W. Minor, " 
 Processing of X-ray Diffraction Data Collected in Oscillation Mode ", 
 Methods in Enzymology, Volume 276: Macromolecular Crystallography, 
 part A, p.307-326, 1997,C.W. Carter, Jr. & R. M. Sweet, Eds., Academic Press.
;
_computing_structure_solution    
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_computing_structure_refinement  
;
 SHELXL97 -Program for Crystal Structure Analysis (Release 97-2). 
 Sheldrick, G.M., Institüt für Anorganische Chemie der Universität, 
 Tammanstrasse 4, D-3400 Göttingen, Germany, 1998 
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;

_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)+(0.0396P)²+0.2118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7141
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0712
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.47717(2) 0.659322(19) 0.329061(12) 0.01975(6) Uani 1 1 d . . .
Co2 Co 0.28583(2) 0.48808(2) 0.363058(12) 0.02029(6) Uani 1 1 d . . .
O1 O 0.91838(12) 0.28927(11) 0.28417(7) 0.0265(2) Uani 1 1 d . . .
O2 O 0.69010(13) -0.00303(12) 0.19900(7) 0.0313(2) Uani 1 1 d . . .
O3 O 0.47088(12) 0.32723(11) 0.19334(6) 0.0218(2) Uani 1 1 d . . .
O4 O 0.81336(14) 0.68217(15) 0.32009(10) 0.0489(4) Uani 1 1 d . . .
O5 O 0.34474(16) 0.83780(15) 0.16914(8) 0.0448(3) Uani 1 1 d . . .
O6 O 0.36658(16) 0.86401(13) 0.45103(8) 0.0388(3) Uani 1 1 d . . .
O7 O 0.08912(15) 0.55827(17) 0.20953(8) 0.0472(3) Uani 1 1 d . . .
O8 O 0.08929(15) 0.66529(16) 0.47716(9) 0.0482(3) Uani 1 1 d . . .
O9 O 0.22172(16) 0.19564(14) 0.44602(10) 0.0510(4) Uani 1 1 d . . .
C1 C 0.82416(16) 0.20124(16) 0.33744(9) 0.0229(3) Uani 1 1 d . . .
H1 H 0.7921 0.2503 0.3876 0.028 Uiso 1 1 calc R . .
C2 C 0.67460(16) 0.18776(14) 0.28883(9) 0.0191(3) Uani 1 1 d . . .
C3 C 0.73647(16) 0.10799(15) 0.21435(9) 0.0225(3) Uani 1 1 d . . .
C4 C 0.86812(18) 0.17069(17) 0.16643(10) 0.0271(3) Uani 1 1 d . . .
H4 H 0.8210 0.2760 0.1383 0.033 Uiso 1 1 calc R . .
C5 C 0.99327(18) 0.18541(18) 0.23017(11) 0.0301(3) Uani 1 1 d . . .
H5 H 1.0847 0.2232 0.2012 0.036 Uiso 1 1 calc R . .
C6 C 1.05248(19) 0.0364(2) 0.28965(12) 0.0376(4) Uani 1 1 d . . .
H6A H 1.1634 0.0295 0.3083 0.045 Uiso 1 1 calc R . .
H6B H 1.0469 -0.0532 0.2628 0.045 Uiso 1 1 calc R . .
C7 C 0.93770(19) 0.04674(17) 0.36277(11) 0.0316(3) Uani 1 1 d . . .
H7A H 0.9956 0.0447 0.4152 0.038 Uiso 1 1 calc R . .
H7B H 0.8790 -0.0381 0.3697 0.038 Uiso 1 1 calc R . .
C8 C 0.56898(17) 0.09668(15) 0.34203(9) 0.0241(3) Uani 1 1 d . . .
H8A H 0.5309 0.1484 0.3891 0.036 Uiso 1 1 calc R . .
H8B H 0.6300 -0.0054 0.3627 0.036 Uiso 1 1 calc R . .
H8C H 0.4779 0.0882 0.3086 0.036 Uiso 1 1 calc R . .
C9 C 0.9382(2) 0.0786(2) 0.09889(12) 0.0419(4) Uani 1 1 d . . .
H9A H 1.0225 0.1248 0.0705 0.063 Uiso 1 1 calc R . .
H9B H 0.8544 0.0784 0.0586 0.063 Uiso 1 1 calc R . .
H9C H 0.9828 -0.0264 0.1243 0.063 Uiso 1 1 calc R . .
C11 C 0.58082(15) 0.34987(14) 0.25258(8) 0.0179(3) Uani 1 1 d . . .
H11 H 0.6574 0.4081 0.2223 0.022 Uiso 1 1 calc R . .
C12 C 0.50069(15) 0.44018(14) 0.31716(9) 0.0184(3) Uani 1 1 d . . .
C13 C 0.50937(16) 0.45873(15) 0.39669(9) 0.0198(3) Uani 1 1 d . . .
H13 H 0.5759 0.4056 0.4465 0.024 Uiso 1 1 calc R . .
C14 C 0.68236(19) 0.67702(16) 0.32129(11) 0.0297(3) Uani 1 1 d . . .
C15 C 0.39810(18) 0.76906(17) 0.22986(10) 0.0281(3) Uani 1 1 d . . .
C16 C 0.41054(18) 0.78779(16) 0.40286(10) 0.0262(3) Uani 1 1 d . . .
C17 C 0.16268(18) 0.52884(19) 0.26852(10) 0.0303(3) Uani 1 1 d . . .
C18 C 0.16519(18) 0.59793(18) 0.43298(10) 0.0291(3) Uani 1 1 d . . .
C19 C 0.24531(18) 0.30726(18) 0.41096(11) 0.0327(4) Uani 1 1 d . . .
C21 C 0.43828(17) 0.44601(16) 0.12347(9) 0.0234(3) Uani 1 1 d . . .
H21A H 0.5383 0.4774 0.1038 0.028 Uiso 1 1 calc R . .
H21B H 0.3656 0.5357 0.1395 0.028 Uiso 1 1 calc R . .
C22 C 0.36271(17) 0.38814(16) 0.05545(9) 0.0233(3) Uani 1 1 d . . .
C23 C 0.23333(17) 0.47935(17) 0.01025(10) 0.0261(3) Uani 1 1 d . . .
H23 H 0.1884 0.5762 0.0247 0.031 Uiso 1 1 calc R . .
C24 C 0.16893(18) 0.43013(18) -0.05604(10) 0.0298(3) Uani 1 1 d . . .
H24 H 0.0808 0.4937 -0.0868 0.036 Uiso 1 1 calc R . .
C25 C 0.2324(2) 0.28935(19) -0.07742(10) 0.0328(3) Uani 1 1 d . . .
H25 H 0.1885 0.2557 -0.1227 0.039 Uiso 1 1 calc R . .
C26 C 0.3603(2) 0.1979(2) -0.03229(12) 0.0398(4) Uani 1 1 d . . .
H26 H 0.4046 0.1009 -0.0467 0.048 Uiso 1 1 calc R . .
C27 C 0.4247(2) 0.24641(19) 0.03395(11) 0.0358(4) Uani 1 1 d . . .
H27 H 0.5121 0.1820 0.0649 0.043 Uiso 1 1 calc R . .


_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 C14 1.7992(16) . ?
Co1 C16 1.8124(15) . ?
Co1 C15 1.8236(16) . ?
Co1 C13 1.9444(13) . ?
Co1 C12 1.9952(13) . ?
Co1 Co2 2.4731(3) . ?
Co2 C19 1.7979(17) . ?
Co2 C18 1.8103(15) . ?
Co2 C17 1.8271(16) . ?
Co2 C13 1.9565(14) . ?
Co2 C12 1.9734(13) . ?
O1 C1 1.4362(18) . ?
O1 C5 1.4415(18) . ?
O2 C3 1.2126(17) . ?
O3 C11 1.4228(16) . ?
O3 C21 1.4289(17) . ?
O4 C14 1.1333(19) . ?
O5 C15 1.133(2) . ?
O6 C16 1.1376(19) . ?
O7 C17 1.124(2) . ?
O8 C18 1.1328(19) . ?
O9 C19 1.135(2) . ?
C1 C7 1.5402(19) . ?
C1 C2 1.5511(19) . ?
C1 H1 1.0000 . ?
C2 C8 1.5180(19) . ?
C2 C3 1.5438(19) . ?
C2 C11 1.5590(18) . ?
C3 C4 1.516(2) . ?
C4 C9 1.530(2) . ?
C4 C5 1.542(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.535(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.538(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 C12 1.5093(18) . ?
C11 H11 1.0000 . ?
C12 C13 1.338(2) . ?
C13 H13 1.0000 . ?
C21 C22 1.502(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.386(2) . ?
C22 C23 1.388(2) . ?
C23 C24 1.391(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.387(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

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
C14 Co1 C16 99.74(7) . . ?
C14 Co1 C15 100.57(7) . . ?
C16 Co1 C15 103.52(7) . . ?
C14 Co1 C13 97.84(6) . . ?
C16 Co1 C13 103.51(6) . . ?
C15 Co1 C13 143.97(6) . . ?
C14 Co1 C12 99.46(6) . . ?
C16 Co1 C12 140.54(6) . . ?
C15 Co1 C12 106.37(6) . . ?
C13 Co1 C12 39.68(6) . . ?
C14 Co1 Co2 147.08(5) . . ?
C16 Co1 Co2 97.97(5) . . ?
C15 Co1 Co2 101.95(5) . . ?
C13 Co1 Co2 50.87(4) . . ?
C12 Co1 Co2 51.06(4) . . ?
C19 Co2 C18 95.30(7) . . ?
C19 Co2 C17 102.16(8) . . ?
C18 Co2 C17 103.04(7) . . ?
C19 Co2 C13 99.11(7) . . ?
C18 Co2 C13 108.70(6) . . ?
C17 Co2 C13 139.64(6) . . ?
C19 Co2 C12 104.99(6) . . ?
C18 Co2 C12 144.21(6) . . ?
C17 Co2 C12 101.11(6) . . ?
C13 Co2 C12 39.80(6) . . ?
C19 Co2 Co1 149.46(5) . . ?
C18 Co2 Co1 97.18(5) . . ?
C17 Co2 Co1 101.98(5) . . ?
C13 Co2 Co1 50.44(4) . . ?
C12 Co2 Co1 51.85(4) . . ?
C1 O1 C5 103.57(11) . . ?
C11 O3 C21 114.61(10) . . ?
O1 C1 C7 103.70(12) . . ?
O1 C1 C2 109.46(11) . . ?
C7 C1 C2 112.85(11) . . ?
O1 C1 H1 110.2 . . ?
C7 C1 H1 110.2 . . ?
C2 C1 H1 110.2 . . ?
C8 C2 C3 110.38(11) . . ?
C8 C2 C1 112.09(12) . . ?
C3 C2 C1 106.15(11) . . ?
C8 C2 C11 111.17(11) . . ?
C3 C2 C11 107.05(11) . . ?
C1 C2 C11 109.76(10) . . ?
O2 C3 C4 122.66(13) . . ?
O2 C3 C2 122.06(13) . . ?
C4 C3 C2 115.11(11) . . ?
C3 C4 C9 113.60(13) . . ?
C3 C4 C5 107.56(13) . . ?
C9 C4 C5 113.34(13) . . ?
C3 C4 H4 107.3 . . ?
C9 C4 H4 107.3 . . ?
C5 C4 H4 107.3 . . ?
O1 C5 C6 103.68(13) . . ?
O1 C5 C4 108.53(11) . . ?
C6 C5 C4 112.96(13) . . ?
O1 C5 H5 110.5 . . ?
C6 C5 H5 110.5 . . ?
C4 C5 H5 110.5 . . ?
C5 C6 C7 103.71(12) . . ?
C5 C6 H6A 111.0 . . ?
C7 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
C7 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C6 C7 C1 103.47(13) . . ?
C6 C7 H7A 111.1 . . ?
C1 C7 H7A 111.1 . . ?
C6 C7 H7B 111.1 . . ?
C1 C7 H7B 111.1 . . ?
H7A C7 H7B 109.0 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C11 C12 112.48(10) . . ?
O3 C11 C2 105.78(10) . . ?
C12 C11 C2 114.19(11) . . ?
O3 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
C2 C11 H11 108.1 . . ?
C13 C12 C11 143.46(12) . . ?
C13 C12 Co2 69.42(8) . . ?
C11 C12 Co2 137.29(9) . . ?
C13 C12 Co1 68.12(8) . . ?
C11 C12 Co1 131.92(9) . . ?
Co2 C12 Co1 77.09(5) . . ?
C12 C13 Co1 72.21(8) . . ?
C12 C13 Co2 70.78(8) . . ?
Co1 C13 Co2 78.69(5) . . ?
C12 C13 H13 135.9 . . ?
Co1 C13 H13 135.9 . . ?
Co2 C13 H13 135.9 . . ?
O4 C14 Co1 176.25(16) . . ?
O5 C15 Co1 178.04(15) . . ?
O6 C16 Co1 177.36(13) . . ?
O7 C17 Co2 177.60(16) . . ?
O8 C18 Co2 179.28(16) . . ?
O9 C19 Co2 175.56(17) . . ?
O3 C21 C22 108.82(11) . . ?
O3 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
O3 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C27 C22 C23 118.71(14) . . ?
C27 C22 C21 120.96(13) . . ?
C23 C22 C21 120.26(13) . . ?
C22 C23 C24 120.53(14) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 120.32(14) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.32(15) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C25 C26 C27 120.54(15) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C22 C27 C26 120.56(15) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        30.10
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.067
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
_chemical_properties_physical    
Air-sensitive,Heat-sensitive,Oxygen-sensitive,Light-sensitive,Photo-sensitive
