# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_t
_database_code_depnum_ccdc_archive 'CCDC 1417644'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-10-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 Dy N2 O14'
_chemical_formula_sum            'C9 H15 Dy N2 O14'
_chemical_formula_weight         537.73

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'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.1045(5)
_cell_length_b                   15.4994(7)
_cell_length_c                   10.4754(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.2070(5)
_cell_angle_gamma                90.00
_cell_volume                     1603.50(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    16654
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      29.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_crystal_density_meas      2.227
_exptl_crystal_density_diffrn    2.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1044
_exptl_absorpt_coefficient_mu    4.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2659
_exptl_absorpt_correction_T_max  0.2877
_exptl_absorpt_process_details   'SADABS, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(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  'Bruker ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16654
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0133
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3271
_reflns_number_gt                3134
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'ApexII (Bruker, 2011)'
_computing_cell_refinement       'ApexII (Bruker, 2011)'
_computing_data_reduction        'ApexII (Bruker, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_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 > 2sigma(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)+(0.0135P)²+2.8918P] 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         3271
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.006
_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 1.085806(13) 1.002599(7) 0.310936(12) 0.00933(6) Uani 1 1 d . . .
O1 O 0.9946(2) 1.13152(13) 0.3714(2) 0.0204(5) Uani 1 1 d . . .
O2 O 0.90206(13) 1.11347(8) 0.54527(12) 0.0230(5) Uani 1 1 d . . .
O1W O 0.93574(13) 1.07384(8) 0.12573(12) 0.0204(5) Uani 1 1 d R . .
HAW1 H 0.9051 1.0488 0.0533 0.025 Uiso 1 1 d R . .
HBW1 H 0.8648 1.0976 0.1409 0.025 Uiso 1 1 d R . .
O2W O 1.02051(13) 0.87706(8) 0.17393(12) 0.0207(5) Uani 1 1 d R . .
HAW2 H 1.0788 0.8475 0.1452 0.025 Uiso 1 1 d R . .
HBW2 H 0.9754 0.8395 0.2058 0.025 Uiso 1 1 d R . .
O3 O 0.72876(16) 1.38294(10) 0.73745(15) 0.0198(5) Uani 1 1 d . . .
O3W O 1.30560(16) 0.93183(10) 0.32747(15) 0.0237(5) Uani 1 1 d R . .
HAW3 H 1.3454 0.9150 0.4031 0.028 Uiso 1 1 d R . .
HBW3 H 1.3076 0.8892 0.2769 0.028 Uiso 1 1 d R . .
O4 O 0.6789(2) 1.49292(13) 0.6036(2) 0.0182(5) Uani 1 1 d . . .
O5 O 0.7352(2) 1.45239(15) 0.0038(2) 0.0207(5) Uani 1 1 d . . .
O6 O 0.6404(2) 1.46371(15) 0.1785(2) 0.0206(5) Uani 1 1 d . . .
O7 O 0.5915(3) 1.22242(19) 0.2604(3) 0.0413(7) Uani 1 1 d . . .
O8 O 0.6542(5) 1.1192(2) 0.1507(5) 0.0752(13) Uani 1 1 d . . .
O9 O 0.7021(4) 1.2493(2) 0.1112(3) 0.0532(9) Uani 1 1 d . . .
N1 N 0.8663(2) 1.38184(16) 0.3303(2) 0.0125(5) Uani 1 1 d . . .
N2 N 0.6496(3) 1.1960(2) 0.1741(3) 0.0275(6) Uani 1 1 d . . .
C1 C 0.9064(3) 1.29866(18) 0.3425(3) 0.0128(5) Uani 1 1 d . . .
H1A H 0.9457 1.2738 0.2787 0.015 Uiso 1 1 calc R . .
C2 C 0.8900(3) 1.25030(18) 0.4478(3) 0.0134(6) Uani 1 1 d . . .
C3 C 0.8313(3) 1.28849(19) 0.5431(3) 0.0141(6) Uani 1 1 d . . .
H3A H 0.8170 1.2563 0.6139 0.017 Uiso 1 1 calc R . .
C4 C 0.7946(3) 1.37491(18) 0.5314(3) 0.0135(5) Uani 1 1 d . . .
C5 C 0.8132(3) 1.42064(18) 0.4233(3) 0.0140(5) Uani 1 1 d . . .
H5A H 0.7889 1.4786 0.4146 0.017 Uiso 1 1 calc R . .
C6 C 0.9332(3) 1.15660(18) 0.4563(3) 0.0137(5) Uani 1 1 d . . .
C7 C 0.7304(3) 1.41978(19) 0.6308(3) 0.0138(6) Uani 1 1 d . . .
C8 C 0.8750(3) 1.4292(2) 0.2097(3) 0.0155(6) Uani 1 1 d . . .
H8A H 0.9270 1.3952 0.1599 0.019 Uiso 1 1 calc R . .
H8B H 0.9228 1.4830 0.2332 0.019 Uiso 1 1 calc R . .
C9 C 0.73611(17) 1.44857(11) 0.12414(16) 0.0135(5) Uani 1 1 d . . .
O5W O 0.51072(17) 1.10949(11) 0.44427(16) 0.0579(10) Uani 1 1 d R . .
HAW5 H 0.5248 1.1440 0.3751 0.069 Uiso 1 1 d R . .
HBW5 H 0.4263 1.0996 0.4324 0.069 Uiso 1 1 d R . .
O4W O 0.74216(17) 1.21307(11) -0.14722(16) 0.0377(6) Uani 1 1 d R . .
HAW4 H 0.7222 1.2208 -0.0732 0.045 Uiso 1 1 d R . .
HBW4 H 0.7288 1.2630 -0.1809 0.045 Uiso 1 1 d R . .


_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 O2 2.3329(12) 3_776 ?
Dy1 O1 2.343(2) . ?
Dy1 O5 2.358(2) 4_686 ?
Dy1 O6 2.388(2) 2_645 ?
Dy1 O2W 2.4250(13) . ?
Dy1 O3W 2.4501(15) . ?
Dy1 O1W 2.4574(13) . ?
Dy1 O3 2.5094(15) 4_685 ?
Dy1 O4 2.544(2) 4_685 ?
Dy1 C7 2.883(3) 4_685 ?
O1 C6 1.249(4) . ?
O2 C6 1.240(3) . ?
O2 Dy1 2.3329(12) 3_776 ?
O1W HAW1 0.8500 . ?
O1W HBW1 0.8499 . ?
O2W HAW2 0.8500 . ?
O2W HBW2 0.8500 . ?
O3 C7 1.258(3) . ?
O3 Dy1 2.5094(15) 4_586 ?
O3W HAW3 0.8499 . ?
O3W HBW3 0.8502 . ?
O4 C7 1.255(3) . ?
O4 Dy1 2.544(2) 4_586 ?
O5 C9 1.260(3) . ?
O5 Dy1 2.358(2) 4_585 ?
O6 C9 1.245(3) . ?
O6 Dy1 2.388(2) 2_655 ?
O7 N2 1.247(4) . ?
O8 N2 1.218(4) . ?
O9 N2 1.244(4) . ?
N1 C1 1.349(4) . ?
N1 C5 1.349(4) . ?
N1 C8 1.479(3) . ?
C1 C2 1.372(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.396(4) . ?
C2 C6 1.514(4) . ?
C3 C4 1.388(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.382(4) . ?
C4 C7 1.508(4) . ?
C5 H5A 0.9300 . ?
C7 Dy1 2.883(3) 4_586 ?
C8 C9 1.527(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O5W HAW5 0.9349 . ?
O5W HBW5 0.8500 . ?
O4W HAW4 0.8501 . ?
O4W HBW4 0.8500 . ?

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
O2 Dy1 O1 116.93(6) 3_776 . ?
O2 Dy1 O5 74.82(6) 3_776 4_686 ?
O1 Dy1 O5 74.53(8) . 4_686 ?
O2 Dy1 O6 72.28(6) 3_776 2_645 ?
O1 Dy1 O6 76.56(8) . 2_645 ?
O5 Dy1 O6 118.73(8) 4_686 2_645 ?
O2 Dy1 O2W 74.57(5) 3_776 . ?
O1 Dy1 O2W 140.43(7) . . ?
O5 Dy1 O2W 142.13(6) 4_686 . ?
O6 Dy1 O2W 71.44(6) 2_645 . ?
O2 Dy1 O3W 71.70(5) 3_776 . ?
O1 Dy1 O3W 139.93(7) . . ?
O5 Dy1 O3W 70.44(7) 4_686 . ?
O6 Dy1 O3W 138.21(7) 2_645 . ?
O2W Dy1 O3W 79.1 . . ?
O2 Dy1 O1W 142.72(2) 3_776 . ?
O1 Dy1 O1W 67.54(6) . . ?
O5 Dy1 O1W 136.06(6) 4_686 . ?
O6 Dy1 O1W 73.33(6) 2_645 . ?
O2W Dy1 O1W 81.3 . . ?
O3W Dy1 O1W 131.0 . . ?
O2 Dy1 O3 142.02(5) 3_776 4_685 ?
O1 Dy1 O3 76.41(7) . 4_685 ?
O5 Dy1 O3 75.39(7) 4_686 4_685 ?
O6 Dy1 O3 144.20(7) 2_645 4_685 ?
O2W Dy1 O3 119.21(5) . 4_685 ?
O3W Dy1 O3 76.48(7) . 4_685 ?
O1W Dy1 O3 74.89(5) . 4_685 ?
O2 Dy1 O4 126.44(6) 3_776 4_685 ?
O1 Dy1 O4 116.44(7) . 4_685 ?
O5 Dy1 O4 115.99(8) 4_686 4_685 ?
O6 Dy1 O4 125.21(8) 2_645 4_685 ?
O2W Dy1 O4 67.67(5) . 4_685 ?
O3W Dy1 O4 65.12(6) . 4_685 ?
O1W Dy1 O4 65.89(6) . 4_685 ?
O3 Dy1 O4 51.54(6) 4_685 4_685 ?
O2 Dy1 C7 141.24(7) 3_776 4_685 ?
O1 Dy1 C7 95.97(8) . 4_685 ?
O5 Dy1 C7 96.66(8) 4_686 4_685 ?
O6 Dy1 C7 139.29(8) 2_645 4_685 ?
O2W Dy1 C7 93.42(6) . 4_685 ?
O3W Dy1 C7 69.86(7) . 4_685 ?
O1W Dy1 C7 67.00(6) . 4_685 ?
O3 Dy1 C7 25.81(7) 4_685 4_685 ?
O4 Dy1 C7 25.78(7) 4_685 4_685 ?
C6 O1 Dy1 137.81(19) . . ?
C6 O2 Dy1 156.03(16) . 3_776 ?
Dy1 O1W HAW1 123.2 . . ?
Dy1 O1W HBW1 116.8 . . ?
HAW1 O1W HBW1 101.6 . . ?
Dy1 O2W HAW2 121.3 . . ?
Dy1 O2W HBW2 114.7 . . ?
HAW2 O2W HBW2 103.9 . . ?
C7 O3 Dy1 93.91(15) . 4_586 ?
Dy1 O3W HAW3 116.5 . . ?
Dy1 O3W HBW3 116.4 . . ?
HAW3 O3W HBW3 105.9 . . ?
C7 O4 Dy1 92.36(17) . 4_586 ?
C9 O5 Dy1 137.65(16) . 4_585 ?
C9 O6 Dy1 155.90(17) . 2_655 ?
C1 N1 C5 121.0(2) . . ?
C1 N1 C8 119.0(2) . . ?
C5 N1 C8 120.0(2) . . ?
O8 N2 O9 120.3(4) . . ?
O8 N2 O7 120.8(4) . . ?
O9 N2 O7 119.0(3) . . ?
N1 C1 C2 120.9(3) . . ?
N1 C1 H1A 119.6 . . ?
C2 C1 H1A 119.6 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 C6 119.3(2) . . ?
C3 C2 C6 121.7(3) . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 C7 118.8(3) . . ?
C3 C4 C7 122.0(3) . . ?
N1 C5 C4 120.5(3) . . ?
N1 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
O2 C6 O1 127.6(3) . . ?
O2 C6 C2 116.5(2) . . ?
O1 C6 C2 115.9(2) . . ?
O4 C7 O3 121.9(3) . . ?
O4 C7 C4 118.6(3) . . ?
O3 C7 C4 119.5(2) . . ?
O4 C7 Dy1 61.86(15) . 4_586 ?
O3 C7 Dy1 60.28(13) . 4_586 ?
C4 C7 Dy1 174.9(2) . 4_586 ?
N1 C8 C9 112.7(2) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O6 C9 O5 127.4(2) . . ?
O6 C9 C8 118.39(19) . . ?
O5 C9 C8 114.06(19) . . ?
HAW5 O5W HBW5 107.6 . . ?
HAW4 O4W HBW4 101.7 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.898
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.112
