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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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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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#  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:
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data_08-1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C72 H36 N12 O32 Zr6'
_chemical_formula_weight         2128.45

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'
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'
Zr Zr -2.9673 0.5597 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           cubic
_symmetry_space_group_name_H-M   Fm-3

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

_cell_length_a                   26.5460(19)
_cell_length_b                   26.5460(19)
_cell_length_c                   26.5460(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     18707(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4192
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9647
_exptl_absorpt_correction_T_max  0.9647
_exptl_absorpt_process_details   saddabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_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            12442
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1491
_reflns_number_gt                1102
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'bruker smart'
_computing_cell_refinement       'bruker smart'
_computing_data_reduction        'bruker saint'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'bruker shelxtl'
_computing_publication_material  'bruker shelxtl'

_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^)+(0.1000P)^2^+0.0933P] 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         1491
_refine_ls_number_parameters     46
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.076
_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
Zr1 Zr 0.09341(3) 1.0000 0.5000 0.0234(3) Uani 1 4 d S . .
O1 O 0.04630(18) 1.04630(18) 0.45370(18) 0.070(2) Uani 1 3 d S . .
O2 O 0.1372(2) 0.9299(2) 0.5000 0.0720(18) Uani 1 2 d S . .
O3 O 0.1367(2) 1.0000 0.4292(2) 0.0746(19) Uani 1 2 d S . .
C1 C 0.1191(4) 0.8830(5) 0.5000 0.105(4) Uani 1 2 d S . .
C2 C 0.1577(5) 0.8412(5) 0.5000 0.161(3) Uani 1 2 d S . .
N1 N 0.2456(5) 0.8197(5) 0.5000 0.160(5) Uani 1 2 d SU . .
C6 C 0.2093(5) 0.8571(5) 0.5000 0.161(3) Uani 1 2 d S . .
H6 H 0.2180 0.8910 0.5000 0.194 Uiso 1 2 calc SR . .
C3 C 0.1439(5) 0.7916(5) 0.5000 0.161(3) Uani 1 2 d S . .
H3 H 0.1100 0.7827 0.5000 0.194 Uiso 1 2 calc SR . .
C4 C 0.1805(4) 0.7548(5) 0.5000 0.161(3) Uani 1 2 d S . .
H4 H 0.1715 0.7210 0.5000 0.194 Uiso 1 2 calc SR . .
C5 C 0.2295(4) 0.7684(5) 0.5000 0.161(3) Uani 1 2 d S . .

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
Zr1 0.0121(5) 0.0295(5) 0.0287(5) 0.000 0.000 0.000
O1 0.070(2) 0.070(2) 0.070(2) -0.043(3) -0.043(3) 0.043(3)
O2 0.066(4) 0.062(4) 0.088(5) 0.000 0.000 0.040(3)
O3 0.063(4) 0.086(4) 0.075(4) 0.000 0.050(3) 0.000
C1 0.085(9) 0.128(11) 0.104(9) 0.000 0.000 0.079(9)
C2 0.073(4) 0.075(4) 0.336(9) 0.000 0.000 0.036(3)
N1 0.134(7) 0.124(7) 0.221(9) 0.000 0.000 0.045(6)
C6 0.073(4) 0.075(4) 0.336(9) 0.000 0.000 0.036(3)
C3 0.073(4) 0.075(4) 0.336(9) 0.000 0.000 0.036(3)
C4 0.073(4) 0.075(4) 0.336(9) 0.000 0.000 0.036(3)
C5 0.073(4) 0.075(4) 0.336(9) 0.000 0.000 0.036(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
Zr1 O1 2.141(3) 51_575 ?
Zr1 O1 2.141(3) 4_576 ?
Zr1 O1 2.141(3) 50_556 ?
Zr1 O1 2.141(3) . ?
Zr1 O2 2.193(5) 51_575 ?
Zr1 O2 2.193(5) . ?
Zr1 O3 2.203(5) 50_556 ?
Zr1 O3 2.203(5) . ?
Zr1 Zr1 3.5069(10) 77_566 ?
Zr1 Zr1 3.5069(10) 69_665 ?
Zr1 Zr1 3.5069(10) 21_455 ?
Zr1 Zr1 3.5069(10) 29_464 ?
O1 Zr1 2.141(3) 69_665 ?
O1 Zr1 2.141(3) 29_464 ?
O2 C1 1.335(14) . ?
O3 C1 1.384(14) 69_665 ?
C1 O3 1.384(14) 77_566 ?
C1 C2 1.510(14) . ?
C2 C3 1.368(17) . ?
C2 C6 1.433(18) . ?
N1 C6 1.384(14) . ?
N1 C5 1.428(16) . ?
C3 C4 1.377(14) . ?
C4 C5 1.350(16) . ?
C5 C5 1.46(2) 85_566 ?

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 Zr1 O1 70.1(2) 51_575 4_576 ?
O1 Zr1 O1 108.5(4) 51_575 50_556 ?
O1 Zr1 O1 70.1(2) 4_576 50_556 ?
O1 Zr1 O1 70.1(2) 51_575 . ?
O1 Zr1 O1 108.5(4) 4_576 . ?
O1 Zr1 O1 70.1(2) 50_556 . ?
O1 Zr1 O2 142.77(6) 51_575 51_575 ?
O1 Zr1 O2 142.77(6) 4_576 51_575 ?
O1 Zr1 O2 79.8(2) 50_556 51_575 ?
O1 Zr1 O2 79.8(2) . 51_575 ?
O1 Zr1 O2 79.8(2) 51_575 . ?
O1 Zr1 O2 79.8(2) 4_576 . ?
O1 Zr1 O2 142.77(6) 50_556 . ?
O1 Zr1 O2 142.77(6) . . ?
O2 Zr1 O2 116.0(4) 51_575 . ?
O1 Zr1 O3 142.60(6) 51_575 50_556 ?
O1 Zr1 O3 79.4(2) 4_576 50_556 ?
O1 Zr1 O3 79.4(2) 50_556 50_556 ?
O1 Zr1 O3 142.60(6) . 50_556 ?
O2 Zr1 O3 73.95(12) 51_575 50_556 ?
O2 Zr1 O3 73.95(12) . 50_556 ?
O1 Zr1 O3 79.4(2) 51_575 . ?
O1 Zr1 O3 142.60(6) 4_576 . ?
O1 Zr1 O3 142.60(6) 50_556 . ?
O1 Zr1 O3 79.4(2) . . ?
O2 Zr1 O3 73.95(12) 51_575 . ?
O2 Zr1 O3 73.95(12) . . ?
O3 Zr1 O3 117.1(4) 50_556 . ?
O1 Zr1 Zr1 35.03(10) 51_575 77_566 ?
O1 Zr1 Zr1 35.03(10) 4_576 77_566 ?
O1 Zr1 Zr1 89.59(18) 50_556 77_566 ?
O1 Zr1 Zr1 89.59(18) . 77_566 ?
O2 Zr1 Zr1 166.98(18) 51_575 77_566 ?
O2 Zr1 Zr1 76.98(18) . 77_566 ?
O3 Zr1 Zr1 111.66(12) 50_556 77_566 ?
O3 Zr1 Zr1 111.66(12) . 77_566 ?
O1 Zr1 Zr1 35.03(10) 51_575 69_665 ?
O1 Zr1 Zr1 89.59(18) 4_576 69_665 ?
O1 Zr1 Zr1 89.59(18) 50_556 69_665 ?
O1 Zr1 Zr1 35.03(10) . 69_665 ?
O2 Zr1 Zr1 111.99(12) 51_575 69_665 ?
O2 Zr1 Zr1 111.99(12) . 69_665 ?
O3 Zr1 Zr1 166.47(18) 50_556 69_665 ?
O3 Zr1 Zr1 76.47(18) . 69_665 ?
Zr1 Zr1 Zr1 60.0 77_566 69_665 ?
O1 Zr1 Zr1 89.59(18) 51_575 21_455 ?
O1 Zr1 Zr1 35.03(10) 4_576 21_455 ?
O1 Zr1 Zr1 35.03(10) 50_556 21_455 ?
O1 Zr1 Zr1 89.59(18) . 21_455 ?
O2 Zr1 Zr1 111.99(12) 51_575 21_455 ?
O2 Zr1 Zr1 111.99(12) . 21_455 ?
O3 Zr1 Zr1 76.47(18) 50_556 21_455 ?
O3 Zr1 Zr1 166.47(18) . 21_455 ?
Zr1 Zr1 Zr1 60.0 77_566 21_455 ?
Zr1 Zr1 Zr1 90.0 69_665 21_455 ?
O1 Zr1 Zr1 89.59(18) 51_575 29_464 ?
O1 Zr1 Zr1 89.59(18) 4_576 29_464 ?
O1 Zr1 Zr1 35.03(10) 50_556 29_464 ?
O1 Zr1 Zr1 35.03(10) . 29_464 ?
O2 Zr1 Zr1 76.98(18) 51_575 29_464 ?
O2 Zr1 Zr1 166.98(18) . 29_464 ?
O3 Zr1 Zr1 111.66(12) 50_556 29_464 ?
O3 Zr1 Zr1 111.66(12) . 29_464 ?
Zr1 Zr1 Zr1 90.0 77_566 29_464 ?
Zr1 Zr1 Zr1 60.0 69_665 29_464 ?
Zr1 Zr1 Zr1 60.0 21_455 29_464 ?
Zr1 O1 Zr1 109.9(2) 69_665 29_464 ?
Zr1 O1 Zr1 109.9(2) 69_665 . ?
Zr1 O1 Zr1 109.9(2) 29_464 . ?
C1 O2 Zr1 126.9(6) . . ?
C1 O3 Zr1 126.3(6) 69_665 . ?
O2 C1 O3 133.3(8) . 77_566 ?
O2 C1 C2 116.1(10) . . ?
O3 C1 C2 110.5(11) 77_566 . ?
C3 C2 C6 122.6(11) . . ?
C3 C2 C1 121.7(12) . . ?
C6 C2 C1 115.7(11) . . ?
C6 N1 C5 118.4(12) . . ?
N1 C6 C2 117.1(12) . . ?
C2 C3 C4 119.5(12) . . ?
C5 C4 C3 119.5(13) . . ?
C4 C5 N1 122.8(11) . . ?
C4 C5 C5 122.7(16) . 85_566 ?
N1 C5 C5 114.5(15) . 85_566 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.088

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 -0.003 -0.006 -0.004 12789 3714 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 968930'