# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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.
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data_import

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Dy O8'
_chemical_formula_sum            'C23 H21 Dy1 O8'
_chemical_formula_weight         587.5

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'
Dy Dy -0.1892 4.4098 '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  -P1

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

_cell_length_a                   9.6458(2)
_cell_length_b                   10.0989(3)
_cell_length_c                   12.4871(4)
_cell_angle_alpha                95.430(2)
_cell_angle_beta                 104.581(3)
_cell_angle_gamma                97.247(2)
_cell_volume                     1157.65(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    12026
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.684
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             578.00
_exptl_absorpt_coefficient_mu    3.272
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.194
_exptl_absorpt_correction_T_max  0.374
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_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  ?
_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            15495
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         27.53
_reflns_number_total             5308
_reflns_number_gt                4665
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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)+(0.0692P)²+2.0398P] where P=(Fo²+2Fc²)/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_number_reflns         5308
_refine_ls_number_parameters     295
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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
Dy01 Dy 0.75213(2) 0.48209(2) 0.010864(18) 0.04035(10) Uani 1 1 d . . .
O2 O 0.8729(3) 0.4358(4) -0.1186(3) 0.0411(7) Uani 1 1 d . . .
O3 O 0.8557(3) 0.2768(4) 0.0472(3) 0.0425(7) Uani 1 1 d D . .
O4 O 0.9299(3) 0.5463(4) 0.1770(3) 0.0469(8) Uani 1 1 d . . .
O5 O 0.6290(4) 0.6125(4) 0.0959(3) 0.0500(9) Uani 1 1 d . . .
O6 O 0.8605(3) 0.7038(3) -0.0248(3) 0.0417(7) Uani 1 1 d . . .
O7 O 0.6487(3) 0.3497(4) 0.1349(3) 0.0451(8) Uani 1 1 d D . .
O8 O 0.5751(3) 0.3234(3) -0.1101(3) 0.0412(7) Uani 1 1 d . . .
O1 O 0.6413(3) 0.6188(3) -0.1308(3) 0.0398(7) Uani 1 1 d . . .
C010 C 0.5598(4) 0.6886(4) 0.1373(3) 0.0330(8) Uani 1 1 d . . .
C011 C 0.9344(4) 0.4348(4) -0.1948(3) 0.0313(8) Uani 1 1 d . . .
C012 C 0.6415(5) 0.8038(5) 0.2248(4) 0.0379(9) Uani 1 1 d . . .
C013 C 0.8453(5) 0.4085(4) -0.3143(3) 0.0340(8) Uani 1 1 d . . .
C014 C 0.7594(5) 0.8193(5) -0.1771(4) 0.0383(9) Uani 1 1 d . . .
C015 C 0.6139(6) 0.3713(7) -0.4491(5) 0.0615(15) Uani 1 1 d . . .
H015 H 0.5133 0.3609 -0.4655 0.074 Uiso 1 1 calc R . .
C016 C 0.5691(5) 0.8894(5) 0.2753(4) 0.0458(11) Uani 1 1 d . . .
H016 H 0.4682 0.8763 0.2540 0.055 Uiso 1 1 calc R . .
C017 C 0.6431(7) 0.9941(6) 0.3567(5) 0.0575(14) Uani 1 1 d . . .
H017 H 0.5923 1.0502 0.3901 0.069 Uiso 1 1 calc R . .
C018 C 0.6955(5) 0.3918(5) -0.3389(4) 0.0447(11) Uani 1 1 d . . .
H018 H 0.6499 0.3943 -0.2816 0.054 Uiso 1 1 calc R . .
C019 C 0.6687(7) 0.2110(6) 0.1319(6) 0.0585(14) Uani 1 1 d . . .
H01A H 0.6078 0.1586 0.0633 0.070 Uiso 1 1 calc R . .
H01B H 0.6445 0.1732 0.1946 0.070 Uiso 1 1 calc R . .
C020 C 0.8289(6) 0.2106(6) 0.1382(5) 0.0556(14) Uani 1 1 d . . .
H02A H 0.8895 0.2584 0.2088 0.067 Uiso 1 1 calc R . .
H02B H 0.8494 0.1190 0.1312 0.067 Uiso 1 1 calc R . .
C021 C 0.6802(8) 0.3663(7) -0.5346(5) 0.0729(19) Uani 1 1 d . . .
H021 H 0.6250 0.3553 -0.6084 0.088 Uiso 1 1 calc R . .
C022 C 0.7005(6) 0.7928(6) -0.2912(5) 0.0553(13) Uani 1 1 d . . .
H022 H 0.6556 0.7063 -0.3236 0.066 Uiso 1 1 calc R . .
C023 C 0.7917(6) 0.8292(8) 0.2558(6) 0.074(2) Uani 1 1 d . . .
H023 H 0.8439 0.7754 0.2215 0.089 Uiso 1 1 calc R . .
C024 C 0.9109(6) 0.3968(7) -0.3993(5) 0.0601(15) Uani 1 1 d . . .
H024 H 1.0111 0.4017 -0.3828 0.072 Uiso 1 1 calc R . .
C025 C 0.8243(7) 0.9494(5) -0.1305(5) 0.0545(13) Uani 1 1 d . . .
H025 H 0.8663 0.9684 -0.0540 0.065 Uiso 1 1 calc R . .
C026 C 0.7080(8) 0.8934(7) -0.3571(6) 0.0671(17) Uani 1 1 d . . .
H026 H 0.6707 0.8743 -0.4341 0.081 Uiso 1 1 calc R . .
C027 C 0.7921(8) 1.0153(7) 0.3885(6) 0.0700(18) Uani 1 1 d . . .
H027 H 0.8427 1.0847 0.4443 0.084 Uiso 1 1 calc R . .
C028 C 0.7526(5) 0.7085(5) -0.1070(4) 0.0372(9) Uani 1 1 d . . .
C029 C 0.7711(7) 1.0235(6) -0.3088(6) 0.0634(15) Uani 1 1 d . . .
H029 H 0.7750 1.0921 -0.3532 0.076 Uiso 1 1 calc R . .
C030 C 0.8297(9) 0.3778(9) -0.5097(5) 0.080(2) Uani 1 1 d . . .
H030 H 0.8755 0.3728 -0.5668 0.096 Uiso 1 1 calc R . .
C031 C 0.8641(7) 0.9345(10) 0.3378(7) 0.091(3) Uani 1 1 d . . .
H031 H 0.9650 0.9500 0.3584 0.109 Uiso 1 1 calc R . .
C032 C 0.8271(8) 1.0499(6) -0.1963(7) 0.0681(17) Uani 1 1 d . . .
H032 H 0.8678 1.1375 -0.1637 0.082 Uiso 1 1 calc R . .
H88 H 0.940(4) 0.270(9) 0.038(7) 0.102 Uiso 1 1 d D . .
H89 H 0.562(4) 0.356(9) 0.140(7) 0.102 Uiso 1 1 d D . .


_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
Dy01 O5 2.244(3) . ?
Dy01 O2 2.265(3) . ?
Dy01 O8 2.306(3) . ?
Dy01 O4 2.310(3) . ?
Dy01 O3 2.444(3) . ?
Dy01 O7 2.452(3) . ?
Dy01 O1 2.461(3) . ?
Dy01 O6 2.477(3) . ?
Dy01 C028 2.834(5) . ?
O2 C011 1.242(5) . ?
O3 C020 1.432(6) . ?
O4 C011 1.258(5) 2_765 ?
O5 C010 1.238(6) . ?
O6 C028 1.274(6) . ?
O7 C019 1.437(7) . ?
O8 C010 1.246(5) 2_665 ?
O1 C028 1.267(5) . ?
C010 O8 1.246(5) 2_665 ?
C010 C012 1.504(6) . ?
C011 O4 1.258(5) 2_765 ?
C011 C013 1.502(5) . ?
C012 C016 1.380(7) . ?
C012 C023 1.386(7) . ?
C013 C024 1.369(7) . ?
C013 C018 1.384(6) . ?
C014 C022 1.380(7) . ?
C014 C025 1.386(7) . ?
C014 C028 1.490(7) . ?
C015 C018 1.384(7) . ?
C015 C021 1.375(10) . ?
C016 C017 1.379(7) . ?
C017 C027 1.374(9) . ?
C019 C020 1.528(8) . ?
C021 C030 1.384(11) . ?
C022 C026 1.372(9) . ?
C023 C031 1.383(9) . ?
C024 C030 1.385(8) . ?
C025 C032 1.367(9) . ?
C026 C029 1.387(9) . ?
C027 C031 1.347(11) . ?
C029 C032 1.360(10) . ?

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
O5 Dy01 O2 152.87(14) . . ?
O5 Dy01 O8 104.41(12) . . ?
O2 Dy01 O8 81.51(12) . . ?
O5 Dy01 O4 82.58(13) . . ?
O2 Dy01 O4 105.20(12) . . ?
O8 Dy01 O4 151.07(14) . . ?
O5 Dy01 O3 135.18(14) . . ?
O2 Dy01 O3 71.71(12) . . ?
O8 Dy01 O3 79.42(12) . . ?
O4 Dy01 O3 76.30(13) . . ?
O5 Dy01 O7 71.95(14) . . ?
O2 Dy01 O7 134.60(13) . . ?
O8 Dy01 O7 76.20(13) . . ?
O4 Dy01 O7 79.59(12) . . ?
O3 Dy01 O7 65.66(11) . . ?
O5 Dy01 O1 74.96(14) . . ?
O2 Dy01 O1 80.50(12) . . ?
O8 Dy01 O1 78.54(12) . . ?
O4 Dy01 O1 130.04(13) . . ?
O3 Dy01 O1 146.64(12) . . ?
O7 Dy01 O1 131.21(11) . . ?
O5 Dy01 O6 81.56(13) . . ?
O2 Dy01 O6 74.47(12) . . ?
O8 Dy01 O6 128.41(12) . . ?
O4 Dy01 O6 80.08(12) . . ?
O3 Dy01 O6 131.35(11) . . ?
O7 Dy01 O6 148.33(12) . . ?
O1 Dy01 O6 53.13(10) . . ?
O5 Dy01 C028 78.22(14) . . ?
O2 Dy01 C028 74.66(13) . . ?
O8 Dy01 C028 103.12(13) . . ?
O4 Dy01 C028 105.79(14) . . ?
O3 Dy01 C028 145.50(12) . . ?
O7 Dy01 C028 148.78(12) . . ?
O1 Dy01 C028 26.50(11) . . ?
O6 Dy01 C028 26.69(11) . . ?
C011 O2 Dy01 167.7(3) . . ?
C020 O3 Dy01 118.2(3) . . ?
C011 O4 Dy01 129.6(3) 2_765 . ?
C010 O5 Dy01 176.2(4) . . ?
C028 O6 Dy01 92.5(3) . . ?
C019 O7 Dy01 116.9(3) . . ?
C010 O8 Dy01 132.2(3) 2_665 . ?
C028 O1 Dy01 93.4(3) . . ?
O5 C010 O8 123.8(4) . 2_665 ?
O5 C010 C012 118.9(4) . . ?
O8 C010 C012 117.3(4) 2_665 . ?
O2 C011 O4 122.9(4) . 2_765 ?
O2 C011 C013 119.7(4) . . ?
O4 C011 C013 117.4(4) 2_765 . ?
C016 C012 C023 117.7(5) . . ?
C016 C012 C010 121.0(4) . . ?
C023 C012 C010 121.2(5) . . ?
C024 C013 C018 119.5(4) . . ?
C024 C013 C011 120.6(4) . . ?
C018 C013 C011 119.9(4) . . ?
C022 C014 C025 118.8(5) . . ?
C022 C014 C028 119.7(4) . . ?
C025 C014 C028 121.5(5) . . ?
C018 C015 C021 120.6(6) . . ?
C017 C016 C012 121.4(5) . . ?
C016 C017 C027 120.0(6) . . ?
C015 C018 C013 119.8(5) . . ?
O7 C019 C020 105.7(5) . . ?
O3 C020 C019 106.1(4) . . ?
C015 C021 C030 119.4(6) . . ?
C026 C022 C014 120.4(5) . . ?
C031 C023 C012 120.0(6) . . ?
C013 C024 C030 120.8(6) . . ?
C032 C025 C014 120.4(6) . . ?
C022 C026 C029 120.0(6) . . ?
C031 C027 C017 119.3(6) . . ?
O1 C028 O6 120.7(4) . . ?
O1 C028 C014 119.9(4) . . ?
O6 C028 C014 119.3(4) . . ?
O1 C028 Dy01 60.1(2) . . ?
O6 C028 Dy01 60.9(2) . . ?
C014 C028 Dy01 174.0(3) . . ?
C032 C029 C026 119.5(6) . . ?
C024 C030 C021 119.8(6) . . ?
C027 C031 C023 121.6(6) . . ?
C029 C032 C025 120.8(6) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.775
_refine_diff_density_min         -1.527
_refine_diff_density_rms         0.136
_database_code_depnum_ccdc_archive 'CCDC 1004691'
