# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Dycpia
_database_code_depnum_ccdc_archive 'CCDC 1526828'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 Dy N2 O9'
_chemical_formula_weight         607.90

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.3615(3)
_cell_length_b                   10.6240(3)
_cell_length_c                   12.5081(3)
_cell_angle_alpha                79.653(2)
_cell_angle_beta                 89.326(2)
_cell_angle_gamma                66.439(2)
_cell_volume                     1119.27(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    23287
_cell_measurement_theta_min      1.66
_cell_measurement_theta_max      25.18

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             598
_exptl_absorpt_coefficient_mu    3.393
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.430
_exptl_absorpt_correction_T_max  0.562
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX-II CCD'
_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            23287
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.18
_reflns_number_total             4012
_reflns_number_gt                3301
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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 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)+(0.0328P)²+2.4383P] where P=(Fo²+2Fc²)/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         4012
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.64365(3) 0.37288(3) 0.33962(2) 0.02620(10) Uani 1 1 d . . .
O1 O 0.6228(5) 0.5377(4) 0.1721(3) 0.0355(10) Uani 1 1 d . . .
O2 O 0.7466(5) 0.5534(5) 0.3138(3) 0.0430(11) Uani 1 1 d . . .
O3 O 0.7429(5) 1.0774(4) -0.0280(3) 0.0385(11) Uani 1 1 d . . .
O4 O 0.5757(5) 1.4415(4) -0.3664(3) 0.0428(12) Uani 1 1 d . . .
O5 O 0.7415(4) 1.3551(4) -0.4884(3) 0.0328(10) Uani 1 1 d . . .
O6 O 1.1773(5) 0.8715(5) -0.3719(4) 0.0557(14) Uani 1 1 d . . .
O7 O 1.1326(6) 0.7339(5) -0.2418(4) 0.0738(19) Uani 1 1 d . . .
O8 O 0.5128(5) 0.2513(4) 0.4466(3) 0.0424(11) Uani 1 1 d . . .
O9 O 0.4578(5) 0.3570(5) 0.2188(4) 0.0511(12) Uani 1 1 d . . .
N1 N 0.2900(8) 0.2189(9) 0.4573(5) 0.072(2) Uani 1 1 d . . .
N2 N 0.2275(7) 0.5026(6) 0.1277(4) 0.0515(15) Uani 1 1 d . . .
C1 C 0.6909(7) 0.5979(6) 0.2163(5) 0.0326(14) Uani 1 1 d . . .
C2 C 0.7027(7) 0.7252(6) 0.1508(4) 0.0319(14) Uani 1 1 d . . .
C3 C 0.6615(7) 0.7626(7) 0.0405(5) 0.0376(15) Uani 1 1 d . . .
H3A H 0.6230 0.7100 0.0072 0.045 Uiso 1 1 calc R . .
C4 C 0.6771(7) 0.8775(7) -0.0207(5) 0.0380(16) Uani 1 1 d . . .
H4A H 0.6512 0.9007 -0.0953 0.046 Uiso 1 1 calc R . .
C5 C 0.7303(7) 0.9573(6) 0.0277(4) 0.0319(14) Uani 1 1 d . . .
C6 C 0.7643(9) 0.9255(8) 0.1388(5) 0.054(2) Uani 1 1 d . . .
H6A H 0.7956 0.9825 0.1723 0.065 Uiso 1 1 calc R . .
C7 C 0.7519(9) 0.8098(8) 0.1996(5) 0.053(2) Uani 1 1 d . . .
H7A H 0.7767 0.7878 0.2744 0.063 Uiso 1 1 calc R . .
C8 C 0.7921(6) 1.0797(6) -0.1353(4) 0.0292(13) Uani 1 1 d . . .
C9 C 0.7196(6) 1.2001(6) -0.2084(4) 0.0287(13) Uani 1 1 d . . .
H9A H 0.6373 1.2749 -0.1884 0.034 Uiso 1 1 calc R . .
C10 C 0.7694(6) 1.2114(6) -0.3146(4) 0.0263(13) Uani 1 1 d . . .
C11 C 0.6888(6) 1.3458(6) -0.3961(4) 0.0281(13) Uani 1 1 d . . .
C12 C 0.8912(6) 1.0983(6) -0.3435(4) 0.0264(13) Uani 1 1 d . . .
H12A H 0.9244 1.1047 -0.4139 0.032 Uiso 1 1 calc R . .
C13 C 0.9634(6) 0.9755(6) -0.2672(4) 0.0288(13) Uani 1 1 d . . .
C14 C 1.0984(6) 0.8542(6) -0.2956(5) 0.0322(14) Uani 1 1 d . . .
C15 C 0.9128(6) 0.9648(6) -0.1623(4) 0.0313(14) Uani 1 1 d . . .
H15A H 0.9590 0.8823 -0.1114 0.038 Uiso 1 1 calc R . .
C16 C 0.3787(8) 0.2824(8) 0.4747(5) 0.0458(18) Uani 1 1 d . . .
H16A H 0.3374 0.3569 0.5111 0.055 Uiso 1 1 calc R . .
C17 C 0.1265(11) 0.2711(17) 0.4914(9) 0.149(6) Uani 1 1 d . . .
H17A H 0.1145 0.3327 0.5416 0.224 Uiso 1 1 calc R . .
H17B H 0.1041 0.1933 0.5260 0.224 Uiso 1 1 calc R . .
H17C H 0.0555 0.3209 0.4285 0.224 Uiso 1 1 calc R . .
C18 C 0.3419(16) 0.1075(12) 0.3984(11) 0.129(5) Uani 1 1 d . . .
H18A H 0.4473 0.0883 0.3795 0.194 Uiso 1 1 calc R . .
H18B H 0.2754 0.1337 0.3332 0.194 Uiso 1 1 calc R . .
H18C H 0.3380 0.0253 0.4427 0.194 Uiso 1 1 calc R . .
C19 C 0.3785(8) 0.4493(8) 0.1417(5) 0.0483(18) Uani 1 1 d . . .
H19A H 0.4322 0.4833 0.0892 0.058 Uiso 1 1 calc R . .
C20 C 0.1443(10) 0.6108(9) 0.0339(6) 0.073(3) Uani 1 1 d . . .
H20A H 0.2180 0.6327 -0.0112 0.110 Uiso 1 1 calc R . .
H20B H 0.0747 0.6932 0.0584 0.110 Uiso 1 1 calc R . .
H20C H 0.0854 0.5776 -0.0073 0.110 Uiso 1 1 calc R . .
C21 C 0.1351(10) 0.4578(13) 0.2087(8) 0.119(5) Uani 1 1 d . . .
H21A H 0.2037 0.3856 0.2651 0.178 Uiso 1 1 calc R . .
H21B H 0.0716 0.4223 0.1744 0.178 Uiso 1 1 calc R . .
H21C H 0.0692 0.5359 0.2398 0.178 Uiso 1 1 calc 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 O4 2.281(4) 2_675 ?
Dy1 O5 2.294(4) 1_546 ?
Dy1 O8 2.359(4) . ?
Dy1 O7 2.390(4) 2_765 ?
Dy1 O9 2.393(5) . ?
Dy1 O6 2.423(4) 2_765 ?
Dy1 O1 2.431(4) . ?
Dy1 O2 2.441(4) . ?
Dy1 C14 2.782(5) 2_765 ?
Dy1 C1 2.792(6) . ?
O1 C1 1.259(7) . ?
O2 C1 1.262(7) . ?
O3 C5 1.388(7) . ?
O3 C8 1.414(6) . ?
O4 C11 1.249(6) . ?
O4 Dy1 2.281(4) 2_675 ?
O5 C11 1.253(6) . ?
O5 Dy1 2.294(4) 1_564 ?
O6 C14 1.233(7) . ?
O6 Dy1 2.423(4) 2_765 ?
O7 C14 1.248(7) . ?
O7 Dy1 2.390(4) 2_765 ?
O8 C16 1.228(7) . ?
O9 C19 1.240(8) . ?
N1 C16 1.302(9) . ?
N1 C18 1.424(13) . ?
N1 C17 1.491(12) . ?
N2 C19 1.296(8) . ?
N2 C20 1.458(9) . ?
N2 C21 1.463(10) . ?
C1 C2 1.495(8) . ?
C2 C3 1.379(8) . ?
C2 C7 1.388(9) . ?
C3 C4 1.379(9) . ?
C4 C5 1.365(9) . ?
C5 C6 1.379(8) . ?
C6 C7 1.371(10) . ?
C8 C9 1.354(8) . ?
C8 C15 1.384(8) . ?
C9 C10 1.403(7) . ?
C10 C12 1.388(7) . ?
C10 C11 1.511(7) . ?
C12 C13 1.390(7) . ?
C13 C15 1.391(7) . ?
C13 C14 1.495(8) . ?
C14 Dy1 2.782(5) 2_765 ?

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
O4 Dy1 O5 89.50(14) 2_675 1_546 ?
O4 Dy1 O8 80.70(15) 2_675 . ?
O5 Dy1 O8 78.73(15) 1_546 . ?
O4 Dy1 O7 152.40(15) 2_675 2_765 ?
O5 Dy1 O7 105.12(18) 1_546 2_765 ?
O8 Dy1 O7 124.60(16) . 2_765 ?
O4 Dy1 O9 79.59(17) 2_675 . ?
O5 Dy1 O9 151.34(15) 1_546 . ?
O8 Dy1 O9 73.41(16) . . ?
O7 Dy1 O9 96.2(2) 2_765 . ?
O4 Dy1 O6 154.53(15) 2_675 2_765 ?
O5 Dy1 O6 81.23(16) 1_546 2_765 ?
O8 Dy1 O6 74.26(14) . 2_765 ?
O7 Dy1 O6 52.80(15) 2_765 2_765 ?
O9 Dy1 O6 97.36(18) . 2_765 ?
O4 Dy1 O1 79.88(13) 2_675 . ?
O5 Dy1 O1 130.74(15) 1_546 . ?
O8 Dy1 O1 144.12(15) . . ?
O7 Dy1 O1 72.82(14) 2_765 . ?
O9 Dy1 O1 73.60(16) . . ?
O6 Dy1 O1 123.85(13) 2_765 . ?
O4 Dy1 O2 80.79(16) 2_675 . ?
O5 Dy1 O2 77.33(14) 1_546 . ?
O8 Dy1 O2 149.70(15) . . ?
O7 Dy1 O2 79.84(18) 2_765 . ?
O9 Dy1 O2 125.97(15) . . ?
O6 Dy1 O2 119.59(16) 2_765 . ?
O1 Dy1 O2 53.57(14) . . ?
O4 Dy1 C14 176.46(17) 2_675 2_765 ?
O5 Dy1 C14 93.95(15) 1_546 2_765 ?
O8 Dy1 C14 99.20(16) . 2_765 ?
O7 Dy1 C14 26.55(16) 2_765 2_765 ?
O9 Dy1 C14 96.97(17) . 2_765 ?
O6 Dy1 C14 26.26(15) 2_765 2_765 ?
O1 Dy1 C14 98.39(15) . 2_765 ?
O2 Dy1 C14 100.72(17) . 2_765 ?
O4 Dy1 C1 78.10(15) 2_675 . ?
O5 Dy1 C1 104.01(17) 1_546 . ?
O8 Dy1 C1 158.58(15) . . ?
O7 Dy1 C1 75.72(16) 2_765 . ?
O9 Dy1 C1 99.58(18) . . ?
O6 Dy1 C1 127.11(15) 2_765 . ?
O1 Dy1 C1 26.76(15) . . ?
O2 Dy1 C1 26.85(16) . . ?
C14 Dy1 C1 101.77(17) 2_765 . ?
C1 O1 Dy1 92.8(3) . . ?
C1 O2 Dy1 92.3(4) . . ?
C5 O3 C8 118.6(4) . . ?
C11 O4 Dy1 171.2(4) . 2_675 ?
C11 O5 Dy1 133.4(4) . 1_564 ?
C14 O6 Dy1 93.3(4) . 2_765 ?
C14 O7 Dy1 94.5(3) . 2_765 ?
C16 O8 Dy1 134.8(4) . . ?
C19 O9 Dy1 126.1(5) . . ?
C16 N1 C18 121.1(8) . . ?
C16 N1 C17 119.7(9) . . ?
C18 N1 C17 119.0(9) . . ?
C19 N2 C20 121.9(6) . . ?
C19 N2 C21 120.1(6) . . ?
C20 N2 C21 117.9(6) . . ?
O1 C1 O2 121.2(6) . . ?
O1 C1 C2 118.3(5) . . ?
O2 C1 C2 120.5(6) . . ?
O1 C1 Dy1 60.4(3) . . ?
O2 C1 Dy1 60.9(3) . . ?
C2 C1 Dy1 175.5(4) . . ?
C3 C2 C7 118.7(6) . . ?
C3 C2 C1 120.4(6) . . ?
C7 C2 C1 120.9(5) . . ?
C2 C3 C4 120.5(6) . . ?
C5 C4 C3 120.2(6) . . ?
C4 C5 C6 119.9(6) . . ?
C4 C5 O3 123.4(5) . . ?
C6 C5 O3 116.5(6) . . ?
C7 C6 C5 120.0(7) . . ?
C6 C7 C2 120.6(6) . . ?
C9 C8 C15 122.1(5) . . ?
C9 C8 O3 116.9(5) . . ?
C15 C8 O3 120.9(5) . . ?
C8 C9 C10 119.6(5) . . ?
C12 C10 C9 119.5(5) . . ?
C12 C10 C11 120.9(5) . . ?
C9 C10 C11 119.6(5) . . ?
O4 C11 O5 124.2(5) . . ?
O4 C11 C10 117.7(5) . . ?
O5 C11 C10 118.0(5) . . ?
C10 C12 C13 120.0(5) . . ?
C12 C13 C15 120.2(5) . . ?
C12 C13 C14 120.8(5) . . ?
C15 C13 C14 119.0(5) . . ?
O6 C14 O7 119.2(5) . . ?
O6 C14 C13 120.6(5) . . ?
O7 C14 C13 120.1(5) . . ?
O6 C14 Dy1 60.4(3) . 2_765 ?
O7 C14 Dy1 58.9(3) . 2_765 ?
C13 C14 Dy1 177.5(4) . 2_765 ?
C8 C15 C13 118.6(5) . . ?
O8 C16 N1 125.0(7) . . ?
O9 C19 N2 125.8(7) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.18
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.685
_refine_diff_density_rms         0.136
