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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_d
#TrackingRef 'web_deposit_cif_file_0_YabingHe_1366684214.d.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C66 H0 N0 O16 Yb3'
_chemical_formula_weight         1567.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -7.2108 4.4329 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_H-M   P-62c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+y, -x, -z+1/2'
'-y, x-y, z'
'x, y, -z+1/2'
'-x+y, -x, z'
'-y, x-y, -z+1/2'
'y, x, z+1/2'
'x-y, -y, -z'
'-x, -x+y, z+1/2'
'y, x, -z'
'x-y, -y, z+1/2'
'-x, -x+y, -z'

_cell_length_a                   19.8480(2)
_cell_length_b                   19.8480(2)
_cell_length_c                   27.8530(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     9502.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1468
_exptl_absorpt_coefficient_mu    2.816
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            20685
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         67.43
_reflns_number_total             5039
_reflns_number_gt                4364
_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 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^ > 2sigma(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^)+(0.1269P)^2^+3.9875P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(4)
_refine_ls_number_reflns         5039
_refine_ls_number_parameters     134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.2097
_refine_ls_wR_factor_gt          0.1943
_refine_ls_goodness_of_fit_ref   1.230
_refine_ls_restrained_S_all      1.230
_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
Yb1 Yb 0.41967(3) 0.63427(3) 0.2500 0.0689(2) Uani 1 2 d S . .
O1 O 0.3562(6) 0.5426(6) 0.1951(3) 0.116(3) Uani 1 1 d . . .
O2 O 0.2311(6) 0.5098(5) 0.1946(3) 0.119(3) Uani 1 1 d . . .
O3 O 0.3333 0.6667 0.2500 0.124(8) Uani 1 6 d S . .
O4 O 0.5138(10) 0.6022(12) 0.2500 0.162(6) Uani 1 2 d S . .
C1 C 0.2885(10) 0.5028(8) 0.1805(4) 0.110(4) Uani 1 1 d . . .
C2 C 0.2726(7) 0.4434(6) 0.1415(3) 0.093(3) Uani 1 1 d . . .
C3 C 0.1996(8) 0.3986(8) 0.1226(5) 0.105(3) Uani 1 1 d . . .
H3A H 0.1592 0.4055 0.1336 0.126 Uiso 1 1 calc R . .
C4 C 0.1847(7) 0.3441(7) 0.0879(4) 0.101(3) Uani 1 1 d . . .
H4A H 0.1345 0.3139 0.0760 0.121 Uiso 1 1 calc R . .
C5 C 0.2432(6) 0.3340(6) 0.0709(4) 0.091(3) Uani 1 1 d . . .
C6 C 0.3169(7) 0.3792(7) 0.0892(5) 0.113(4) Uani 1 1 d . . .
H6A H 0.3576 0.3730 0.0779 0.136 Uiso 1 1 calc R . .
C7 C 0.3307(7) 0.4340(7) 0.1244(4) 0.111(3) Uani 1 1 d . . .
H7A H 0.3808 0.4647 0.1363 0.133 Uiso 1 1 calc R . .
C8 C 0.2848(6) 0.2848(6) 0.0000 0.095(4) Uani 1 2 d S . .
H8A H 0.3316 0.3316 0.0000 0.113 Uiso 1 2 calc SR . .
C9 C 0.2284(6) 0.2727(6) 0.0342(3) 0.085(2) Uani 1 1 d . . .
C10 C 0.1589(5) 0.2035(5) 0.0331(3) 0.079(2) Uani 1 1 d . . .
H10A H 0.1201 0.1953 0.0550 0.095 Uiso 1 1 calc R . .
C11 C 0.1455(6) 0.1455(6) 0.0000 0.073(3) Uani 1 2 d S . .
C12 C 0.0699(6) 0.0699(6) 0.0000 0.066(2) Uani 1 2 d S . .
C13 C 0.0000 0.0699(6) 0.0000 0.069(3) Uani 1 2 d S . .
H13A H 0.0000 0.1168 0.0000 0.082 Uiso 1 2 calc SR . .

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
Yb1 0.0623(4) 0.0623(3) 0.0803(3) 0.000 0.000 0.0298(3)
O1 0.130(7) 0.106(6) 0.110(5) -0.049(5) -0.034(5) 0.059(5)
O2 0.128(6) 0.099(5) 0.123(6) -0.038(4) 0.019(5) 0.052(5)
O3 0.048(4) 0.048(4) 0.28(3) 0.000 0.000 0.024(2)
O4 0.133(11) 0.190(15) 0.231(18) 0.000 0.000 0.131(12)
C1 0.157(13) 0.087(8) 0.080(6) -0.016(5) 0.000(7) 0.056(8)
C2 0.100(7) 0.085(6) 0.089(5) -0.016(5) 0.003(5) 0.043(6)
C3 0.090(7) 0.096(7) 0.121(8) -0.032(7) 0.009(6) 0.040(6)
C4 0.085(6) 0.087(6) 0.116(7) -0.033(6) 0.002(6) 0.032(5)
C5 0.082(6) 0.074(5) 0.099(6) -0.019(5) 0.014(5) 0.026(5)
C6 0.089(7) 0.098(7) 0.131(8) -0.039(6) 0.010(6) 0.030(6)
C7 0.084(7) 0.107(8) 0.126(8) -0.044(6) -0.005(6) 0.037(6)
C8 0.070(5) 0.070(5) 0.121(10) -0.020(4) 0.020(4) 0.018(6)
C9 0.075(5) 0.076(5) 0.090(5) -0.022(4) 0.010(4) 0.028(4)
C10 0.069(5) 0.074(5) 0.089(5) -0.012(4) 0.016(4) 0.032(4)
C11 0.065(4) 0.065(4) 0.081(6) -0.009(3) 0.009(3) 0.027(5)
C12 0.063(4) 0.063(4) 0.069(5) -0.007(2) 0.007(2) 0.030(5)
C13 0.064(6) 0.068(5) 0.074(5) 0.002(2) 0.005(5) 0.032(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
Yb1 O3 2.1099(6) . ?
Yb1 O2 2.214(7) 6_665 ?
Yb1 O2 2.214(7) 3_665 ?
Yb1 O1 2.223(8) . ?
Yb1 O1 2.223(8) 4 ?
Yb1 O4 2.255(12) . ?
Yb1 Yb1 3.6544(10) 2_565 ?
Yb1 Yb1 3.6544(10) 3_665 ?
O1 C1 1.237(18) . ?
O2 C1 1.277(15) . ?
O2 Yb1 2.214(7) 2_565 ?
O3 Yb1 2.1099(6) 3_665 ?
O3 Yb1 2.1099(6) 2_565 ?
C1 C2 1.515(14) . ?
C2 C7 1.344(16) . ?
C2 C3 1.371(18) . ?
C3 C4 1.368(16) . ?
C3 H3A 0.9300 . ?
C4 C5 1.359(16) . ?
C4 H4A 0.9300 . ?
C5 C6 1.376(17) . ?
C5 C9 1.500(13) . ?
C6 C7 1.387(15) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C8 C9 1.396(11) 10 ?
C8 C9 1.396(11) . ?
C8 H8A 0.9300 . ?
C9 C10 1.377(13) . ?
C10 C11 1.394(10) . ?
C10 H10A 0.9300 . ?
C11 C10 1.394(10) 10 ?
C11 C12 1.500(17) . ?
C12 C13 1.387(8) . ?
C12 C13 1.387(8) 5 ?
C13 C12 1.387(8) 3 ?
C13 H13A 0.9300 . ?

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
O3 Yb1 O2 93.2(2) . 6_665 ?
O3 Yb1 O2 93.2(2) . 3_665 ?
O2 Yb1 O2 88.3(6) 6_665 3_665 ?
O3 Yb1 O1 92.0(3) . . ?
O2 Yb1 O1 174.8(4) 6_665 . ?
O2 Yb1 O1 92.2(4) 3_665 . ?
O3 Yb1 O1 92.0(3) . 4 ?
O2 Yb1 O1 92.2(4) 6_665 4 ?
O2 Yb1 O1 174.8(4) 3_665 4 ?
O1 Yb1 O1 86.9(6) . 4 ?
O3 Yb1 O4 178.8(5) . . ?
O2 Yb1 O4 86.0(4) 6_665 . ?
O2 Yb1 O4 86.0(4) 3_665 . ?
O1 Yb1 O4 88.9(5) . . ?
O1 Yb1 O4 88.9(5) 4 . ?
O3 Yb1 Yb1 30.0 . 2_565 ?
O2 Yb1 Yb1 113.9(2) 6_665 2_565 ?
O2 Yb1 Yb1 113.9(2) 3_665 2_565 ?
O1 Yb1 Yb1 70.6(3) . 2_565 ?
O1 Yb1 Yb1 70.6(3) 4 2_565 ?
O4 Yb1 Yb1 151.2(5) . 2_565 ?
O3 Yb1 Yb1 30.0 . 3_665 ?
O2 Yb1 Yb1 71.9(3) 6_665 3_665 ?
O2 Yb1 Yb1 71.9(3) 3_665 3_665 ?
O1 Yb1 Yb1 113.1(3) . 3_665 ?
O1 Yb1 Yb1 113.1(3) 4 3_665 ?
O4 Yb1 Yb1 148.8(5) . 3_665 ?
Yb1 Yb1 Yb1 60.0 2_565 3_665 ?
C1 O1 Yb1 137.7(8) . . ?
C1 O2 Yb1 134.9(8) . 2_565 ?
Yb1 O3 Yb1 120.0 3_665 2_565 ?
Yb1 O3 Yb1 120.0 3_665 . ?
Yb1 O3 Yb1 120.0 2_565 . ?
O1 C1 O2 124.8(10) . . ?
O1 C1 C2 118.1(13) . . ?
O2 C1 C2 117.1(13) . . ?
C7 C2 C3 118.3(9) . . ?
C7 C2 C1 120.2(12) . . ?
C3 C2 C1 121.5(11) . . ?
C4 C3 C2 121.7(11) . . ?
C4 C3 H3A 119.1 . . ?
C2 C3 H3A 119.1 . . ?
C5 C4 C3 120.0(12) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 118.9(10) . . ?
C4 C5 C9 121.5(10) . . ?
C6 C5 C9 119.5(9) . . ?
C5 C6 C7 120.0(11) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C2 C7 C6 121.0(11) . . ?
C2 C7 H7A 119.5 . . ?
C6 C7 H7A 119.5 . . ?
C9 C8 C9 121.8(12) 10 . ?
C9 C8 H8A 119.1 10 . ?
C9 C8 H8A 119.1 . . ?
C10 C9 C8 118.2(8) . . ?
C10 C9 C5 121.0(8) . . ?
C8 C9 C5 120.7(9) . . ?
C9 C10 C11 121.4(8) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
C10 C11 C10 118.8(11) . 10 ?
C10 C11 C12 120.6(5) . . ?
C10 C11 C12 120.6(5) 10 . ?
C13 C12 C13 120.0(12) . 5 ?
C13 C12 C11 120.0(6) . . ?
C13 C12 C11 120.0(6) 5 . ?
C12 C13 C12 120.0(12) 3 . ?
C12 C13 H13A 120.0 3 . ?
C12 C13 H13A 120.0 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.43
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.740
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.165


_database_code_depnum_ccdc_archive 'CCDC 935253'