# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_aaa
#TrackingRef 'AAA.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C9 H3 Dy O6'
_chemical_formula_sum            'C9 H3 Dy O6'
_chemical_formula_weight         369.61

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'
Dy Dy -0.1892 4.4098 '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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   P4322

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'
'-x, y, -z'
'x, -y, -z+1/2'
'y, x, -z+1/4'
'-y, -x, -z+3/4'

_cell_length_a                   10.3087(15)
_cell_length_b                   10.3087(15)
_cell_length_c                   13.967(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1484.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1283
_cell_measurement_theta_min      7.33
_cell_measurement_theta_max      2.499

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    5.040
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9241
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   Process-auto

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11426
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0301
_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       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         7.33
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1283
_reflns_number_gt                1149
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Process-auto
_computing_cell_refinement       Process-auto
_computing_data_reduction        Process-auto
_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^)+(0.0203P)^2^+2.6911P] 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    none
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(4)
_refine_ls_number_reflns         1283
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0223
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
Dy1 Dy 0.37451(2) 0.37451(2) 0.1250 0.01750(11) Uani 1 2 d S . .
O1 O 0.4182(6) 0.2376(5) 0.2518(3) 0.0504(14) Uani 1 1 d . . .
O3 O 0.4174(5) -0.1844(4) 0.4471(3) 0.0388(12) Uani 1 1 d . . .
O2 O 0.4088(5) 0.4140(4) 0.3351(3) 0.0444(11) Uani 1 1 d . . .
C5 C 0.4260(6) 0.2933(6) 0.3288(4) 0.0311(15) Uani 1 1 d . . .
C2 C 0.4632(7) 0.2196(6) 0.4187(4) 0.0285(13) Uani 1 1 d . . .
C4 C 0.5000 0.0173(9) 0.5000 0.033(2) Uani 1 2 d S . .
C3 C 0.4617(7) 0.0840(6) 0.4179(4) 0.0332(16) Uani 1 1 d . . .
H3 H 0.4356 0.0390 0.3635 0.080 Uiso 1 1 calc . . .
C1 C 0.5000 0.2853(8) 0.5000 0.030(2) Uani 1 2 d S . .
H1 H 0.5000 0.3755 0.5000 0.080 Uiso 1 2 calc S . .
C6 C 0.5000 -0.1283(9) 0.5000 0.035(2) 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
Dy1 0.01890(13) 0.01890(13) 0.01470(15) 0.00035(10) -0.00035(10) 0.00425(15)
O1 0.086(4) 0.050(3) 0.0155(19) 0.001(2) -0.010(2) 0.026(3)
O3 0.075(4) 0.020(2) 0.0221(19) -0.0009(17) -0.017(2) 0.002(2)
O2 0.050(3) 0.023(2) 0.061(3) 0.010(2) -0.026(2) 0.0020(18)
C5 0.039(4) 0.023(3) 0.031(3) 0.008(3) -0.003(3) 0.007(3)
C2 0.054(4) 0.019(3) 0.013(2) 0.000(2) -0.006(3) 0.002(2)
C4 0.056(6) 0.025(5) 0.018(4) 0.000 -0.008(4) 0.000
C3 0.062(5) 0.020(3) 0.017(2) 0.001(2) -0.007(3) 0.000(3)
C1 0.047(6) 0.017(4) 0.026(4) 0.000 -0.003(4) 0.000
C6 0.068(6) 0.021(4) 0.015(3) 0.000 -0.003(4) 0.000

_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
Dy1 O3 2.247(4) 6 ?
Dy1 O3 2.247(4) 3_554 ?
Dy1 O2 2.278(5) 6_565 ?
Dy1 O2 2.278(5) 3_654 ?
Dy1 O1 2.309(4) 7 ?
Dy1 O1 2.309(4) . ?
Dy1 C5 3.014(6) 7 ?
Dy1 C5 3.014(6) . ?
O1 C5 1.221(7) . ?
O3 C6 1.267(6) . ?
O3 Dy1 2.247(4) 4 ?
O2 C5 1.259(7) . ?
O2 Dy1 2.278(5) 4_565 ?
C5 C2 1.517(7) . ?
C2 C1 1.375(6) . ?
C2 C3 1.398(9) . ?
C4 C3 1.394(7) 5_656 ?
C4 C3 1.394(7) . ?
C4 C6 1.501(13) . ?
C3 H3 0.9300 . ?
C1 C2 1.375(6) 5_656 ?
C1 H1 0.9300 . ?
C6 O3 1.267(6) 5_656 ?

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 Dy1 O3 123.0(2) 6 3_554 ?
O3 Dy1 O2 156.01(16) 6 6_565 ?
O3 Dy1 O2 80.64(17) 3_554 6_565 ?
O3 Dy1 O2 80.64(17) 6 3_654 ?
O3 Dy1 O2 156.01(16) 3_554 3_654 ?
O2 Dy1 O2 76.3(2) 6_565 3_654 ?
O3 Dy1 O1 86.95(18) 6 7 ?
O3 Dy1 O1 76.84(15) 3_554 7 ?
O2 Dy1 O1 95.5(2) 6_565 7 ?
O2 Dy1 O1 111.54(17) 3_654 7 ?
O3 Dy1 O1 76.84(15) 6 . ?
O3 Dy1 O1 86.95(18) 3_554 . ?
O2 Dy1 O1 111.54(17) 6_565 . ?
O2 Dy1 O1 95.5(2) 3_654 . ?
O1 Dy1 O1 145.8(3) 7 . ?
O3 Dy1 C5 77.60(16) 6 7 ?
O3 Dy1 C5 98.41(15) 3_554 7 ?
O2 Dy1 C5 96.05(18) 6_565 7 ?
O2 Dy1 C5 90.43(17) 3_654 7 ?
O1 Dy1 C5 21.79(16) 7 7 ?
O1 Dy1 C5 152.41(18) . 7 ?
O3 Dy1 C5 98.41(15) 6 . ?
O3 Dy1 C5 77.60(16) 3_554 . ?
O2 Dy1 C5 90.43(17) 6_565 . ?
O2 Dy1 C5 96.05(18) 3_654 . ?
O1 Dy1 C5 152.41(18) 7 . ?
O1 Dy1 C5 21.79(16) . . ?
C5 Dy1 C5 171.8(3) 7 . ?
C5 O1 Dy1 113.6(4) . . ?
C6 O3 Dy1 142.4(5) . 4 ?
C5 O2 Dy1 169.8(4) . 4_565 ?
O1 C5 O2 121.1(5) . . ?
O1 C5 C2 120.7(5) . . ?
O2 C5 C2 118.1(5) . . ?
O1 C5 Dy1 44.6(3) . . ?
O2 C5 Dy1 76.6(3) . . ?
C2 C5 Dy1 164.9(4) . . ?
C1 C2 C3 120.1(5) . . ?
C1 C2 C5 120.4(5) . . ?
C3 C2 C5 119.4(5) . . ?
C3 C4 C3 120.9(8) 5_656 . ?
C3 C4 C6 119.6(4) 5_656 . ?
C3 C4 C6 119.6(4) . . ?
C4 C3 C2 118.9(6) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C2 C1 C2 121.0(7) . 5_656 ?
C2 C1 H1 119.5 . . ?
C2 C1 H1 119.5 5_656 . ?
O3 C6 O3 125.7(9) . 5_656 ?
O3 C6 C4 117.2(4) . . ?
O3 C6 C4 117.2(4) 5_656 . ?

_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.961
_refine_diff_density_max         1.114
_refine_diff_density_min         -0.351
_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 0.000 0.000 -0.006 684 52 ' '
_platon_squeeze_details          
;
;
_database_code_depnum_ccdc_archive 'CCDC 936103'