# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013


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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 866665'
#TrackingRef '- comp2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H108 O18 Zn12'
_chemical_formula_weight         1830.08
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           Trigonal
_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                   20.4631(2)
_cell_length_b                   20.4631(2)
_cell_length_c                   16.2871(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     5906.3(5)
_cell_formula_units_Z            3
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2397
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485
_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2808
_exptl_absorpt_coefficient_mu    3.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.257
_exptl_absorpt_correction_T_max  0.418
_exptl_absorpt_process_details   'Scalepak (Otwinowski, Minor, 1997)'
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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       '\k-geometry diffractometr'
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'area detector \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2996
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         27.45
_reflns_number_total             2996
_reflns_number_gt                2532
_reflns_threshold_expression     I>2\s(I)
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_data_reduction        'Denzo & Scalepak (Otwinowski, Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
DIAMOND v2.1 (Brandenburg, 1999)
Ortep-3 for Windows, L.J.Farrugia (1997) J.Appl.Cryst. 30, 565,
ORTEP III (Burnett, Johnson, 1996)
;
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 1997),
;
_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0163P)^2^+64.8237P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2996
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0786
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.1867(2) 0.2826(2) 0.0463(2) 0.0308(8) Uani 1 1 d . . .
C2 C 0.1691(3) 0.3316(3) 0.1006(3) 0.0551(13) Uani 1 1 d . . .
H2A H 0.1593 0.3118 0.1555 0.083 Uiso 1 1 calc R . .
H2B H 0.1255 0.3322 0.0799 0.083 Uiso 1 1 calc R . .
H2C H 0.2114 0.3821 0.1011 0.083 Uiso 1 1 calc R . .
C3 C 0.2031(4) 0.3185(3) -0.0397(3) 0.088(3) Uani 1 1 d . . .
H3A H 0.2408 0.3709 -0.0356 0.132 Uiso 1 1 calc R . .
H3B H 0.1577 0.3139 -0.0623 0.132 Uiso 1 1 calc R . .
H3C H 0.2212 0.2932 -0.0747 0.132 Uiso 1 1 calc R . .
C4 C 0.2544(3) 0.2818(3) 0.0793(6) 0.115(4) Uani 1 1 d . . .
H4A H 0.2959 0.3326 0.0830 0.172 Uiso 1 1 calc R . .
H4B H 0.2677 0.2531 0.0433 0.172 Uiso 1 1 calc R . .
H4C H 0.2432 0.2592 0.1329 0.172 Uiso 1 1 calc R . .
C5 C 0.06401(19) 0.17884(19) 0.3405(2) 0.0211(7) Uani 1 1 d . . .
C6 C 0.0148(2) 0.1252(2) 0.4082(2) 0.0306(8) Uani 1 1 d . . .
H6A H 0.0290 0.0875 0.4172 0.046 Uiso 1 1 calc R . .
H6B H -0.0372 0.1012 0.3920 0.046 Uiso 1 1 calc R . .
H6C H 0.0218 0.1531 0.4579 0.046 Uiso 1 1 calc R . .
C7 C 0.0418(3) 0.2393(2) 0.3283(3) 0.0390(10) Uani 1 1 d . . .
H7A H -0.0101 0.2157 0.3117 0.058 Uiso 1 1 calc R . .
H7B H 0.0731 0.2740 0.2866 0.058 Uiso 1 1 calc R . .
H7C H 0.0485 0.2659 0.3789 0.058 Uiso 1 1 calc R . .
C8 C 0.1468(2) 0.2153(2) 0.3659(3) 0.0370(9) Uani 1 1 d . . .
H8A H 0.1543 0.2421 0.4165 0.055 Uiso 1 1 calc R . .
H8B H 0.1779 0.2498 0.3239 0.055 Uiso 1 1 calc R . .
H8C H 0.1601 0.1769 0.3731 0.055 Uiso 1 1 calc R . .
C9 C -0.04906(19) 0.06423(18) 0.1229(2) 0.0190(6) Uani 1 1 d . . .
O1 O 0.01011(13) 0.13085(12) 0.11926(13) 0.0183(5) Uani 1 1 d . . .
O2 O -0.06371(13) 0.03132(13) 0.19273(14) 0.0213(5) Uani 1 1 d . . .
O3 O -0.08980(13) 0.03401(13) 0.05922(13) 0.0195(5) Uani 1 1 d . . .
Zn1 Zn 0.10098(2) 0.17843(2) 0.03977(2) 0.01954(11) Uani 1 1 d . . .
Zn2 Zn 0.04687(2) 0.12283(2) 0.23741(2) 0.02325(11) 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
C1 0.029(2) 0.0177(17) 0.034(2) -0.0040(15) 0.0025(16) 0.0023(15)
C2 0.065(3) 0.027(2) 0.064(3) -0.013(2) 0.003(3) 0.016(2)
C3 0.102(5) 0.048(3) 0.044(3) 0.003(3) 0.019(3) -0.016(3)
C4 0.029(3) 0.037(3) 0.263(11) -0.024(5) -0.049(5) 0.004(2)
C5 0.0233(17) 0.0212(17) 0.0194(15) -0.0032(13) 0.0033(13) 0.0115(14)
C6 0.034(2) 0.032(2) 0.0252(18) 0.0005(15) 0.0054(15) 0.0157(17)
C7 0.053(3) 0.030(2) 0.041(2) 0.0003(18) 0.012(2) 0.027(2)
C8 0.029(2) 0.037(2) 0.033(2) -0.0119(18) -0.0035(17) 0.0083(18)
C9 0.0192(16) 0.0187(16) 0.0201(15) -0.0005(12) 0.0023(12) 0.0102(14)
O1 0.0212(12) 0.0168(11) 0.0151(10) -0.0013(9) -0.0005(9) 0.0081(10)
O2 0.0226(12) 0.0213(12) 0.0175(11) 0.0018(9) 0.0037(9) 0.0092(10)
O3 0.0202(12) 0.0201(12) 0.0164(11) 0.0003(9) -0.0024(9) 0.0088(10)
Zn1 0.0207(2) 0.01520(19) 0.01923(19) -0.00051(14) 0.00050(15) 0.00640(16)
Zn2 0.0291(2) 0.0240(2) 0.01669(18) -0.00566(15) -0.00244(16) 0.01327(18)
_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 C4 1.493(7) . ?
C1 C2 1.510(6) . ?
C1 C3 1.539(7) . ?
C1 Zn1 1.973(4) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.526(5) . ?
C5 C8 1.527(5) . ?
C5 C7 1.529(5) . ?
C5 Zn2 1.963(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O2 1.279(4) . ?
C9 O3 1.279(4) . ?
C9 O1 1.295(4) . ?
C9 Zn2 2.533(3) . ?
O1 Zn1 2.067(2) . ?
O1 Zn2 2.102(2) . ?
O2 Zn2 2.039(2) 2 ?
O2 Zn2 2.218(2) . ?
O3 Zn1 2.048(2) 12 ?
O3 Zn1 2.111(2) 2 ?
Zn1 O3 2.048(2) 11 ?
Zn1 O3 2.111(2) 3 ?
Zn2 O2 2.039(2) 3 ?
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
C4 C1 C2 109.1(5) . . ?
C4 C1 C3 110.6(6) . . ?
C2 C1 C3 106.4(4) . . ?
C4 C1 Zn1 109.7(3) . . ?
C2 C1 Zn1 111.8(3) . . ?
C3 C1 Zn1 109.3(3) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C8 109.1(3) . . ?
C6 C5 C7 108.7(3) . . ?
C8 C5 C7 110.2(3) . . ?
C6 C5 Zn2 109.7(2) . . ?
C8 C5 Zn2 110.3(2) . . ?
C7 C5 Zn2 108.8(3) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 O3 122.8(3) . . ?
O2 C9 O1 116.4(3) . . ?
O3 C9 O1 120.8(3) . . ?
O2 C9 Zn2 61.08(17) . . ?
O3 C9 Zn2 171.5(2) . . ?
O1 C9 Zn2 55.93(15) . . ?
C9 O1 Zn1 132.2(2) . . ?
C9 O1 Zn2 93.38(18) . . ?
Zn1 O1 Zn2 109.72(10) . . ?
C9 O2 Zn2 137.8(2) . 2 ?
C9 O2 Zn2 88.61(19) . . ?
Zn2 O2 Zn2 126.70(11) 2 . ?
C9 O3 Zn1 118.8(2) . 12 ?
C9 O3 Zn1 130.1(2) . 2 ?
Zn1 O3 Zn1 110.90(10) 12 2 ?
C1 Zn1 O3 128.54(13) . 11 ?
C1 Zn1 O1 125.43(13) . . ?
O3 Zn1 O1 92.13(9) 11 . ?
C1 Zn1 O3 117.43(14) . 3 ?
O3 Zn1 O3 91.39(12) 11 3 ?
O1 Zn1 O3 91.99(9) . 3 ?
C5 Zn2 O2 130.80(12) . 3 ?
C5 Zn2 O1 134.73(12) . . ?
O2 Zn2 O1 91.00(9) 3 . ?
C5 Zn2 O2 125.64(12) . . ?
O2 Zn2 O2 88.49(13) 3 . ?
O1 Zn2 O2 60.77(8) . . ?
C5 Zn2 C9 140.92(13) . . ?
O2 Zn2 C9 86.92(10) 3 . ?
O1 Zn2 C9 30.69(10) . . ?
O2 Zn2 C9 30.32(9) . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.761
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.108