# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_xh4-eu
_database_code_depnum_ccdc_archive 'CCDC 976991'
_audit_update_record             
;
2013-12-13 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Eu N O9'
_chemical_formula_sum            'C20 H20 Eu N O9'
_chemical_formula_weight         570.33

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           'Orthorhombic '
_symmetry_space_group_name_H-M   'Pna21 '
_symmetry_space_group_name_Hall  'P 2c -2n  '

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

_cell_length_a                   28.044(2)
_cell_length_b                   9.6262(7)
_cell_length_c                   8.2546(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2228.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3230
_cell_measurement_theta_min      1.46
_cell_measurement_theta_max      26.91

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1128
_exptl_absorpt_coefficient_mu    2.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5465
_exptl_absorpt_correction_T_max  0.8033
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_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 Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15199
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3691
_reflns_number_gt                3178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0164P)²+0.1649P] 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     SHELXL
_refine_ls_extinction_coef       0.00076(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(15)
_refine_ls_number_reflns         3691
_refine_ls_number_parameters     281
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0519
_refine_ls_wR_factor_gt          0.0496
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.002
_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
Eu1 Eu -0.003774(6) 1.414557(19) 0.90702(11) 0.02643(8) Uani 1 1 d . . .
O1 O 0.07212(11) 1.4752(4) 1.0005(4) 0.0462(10) Uani 1 1 d . . .
O2 O 0.06308(13) 1.6105(4) 1.2143(5) 0.0409(10) Uani 1 1 d . . .
O3 O 0.45088(12) 1.8858(3) 0.9656(4) 0.0417(10) Uani 1 1 d . . .
O4 O 0.45931(11) 1.7958(4) 1.2111(4) 0.0375(9) Uani 1 1 d . . .
O5 O 0.22818(14) 1.7770(5) 1.3501(5) 0.0602(14) Uani 1 1 d . . .
O6 O 0.30042(14) 1.5622(5) 1.3161(6) 0.0702(15) Uani 1 1 d U . .
O7 O 0.02162(16) 1.1963(4) 1.0143(5) 0.0554(11) Uani 1 1 d . . .
O8 O -0.02294(12) 1.4121(3) 1.2126(4) 0.0340(8) Uani 1 1 d . . .
O9 O -0.07362(13) 1.3048(4) 1.0523(5) 0.0494(11) Uani 1 1 d . . .
C1 C 0.08804(17) 1.5559(5) 1.1060(7) 0.0330(13) Uani 1 1 d . . .
C2 C 0.13999(16) 1.5917(5) 1.1033(6) 0.0312(12) Uani 1 1 d . . .
C3 C 0.16841(17) 1.5548(5) 0.9725(7) 0.0427(15) Uani 1 1 d . . .
H3A H 0.1558 1.5045 0.8865 0.051 Uiso 1 1 calc R . .
C4 C 0.21595(17) 1.5943(6) 0.9724(7) 0.0438(15) Uani 1 1 d . . .
H4A H 0.2349 1.5704 0.8843 0.053 Uiso 1 1 calc R . .
C5 C 0.23611(17) 1.6677(5) 1.0986(7) 0.0372(14) Uani 1 1 d . . .
C6 C 0.20689(19) 1.7021(6) 1.2317(7) 0.0375(14) Uani 1 1 d . . .
C7 C 0.15893(16) 1.6659(5) 1.2336(6) 0.0310(12) Uani 1 1 d . . .
H7A H 0.1397 1.6909 1.3206 0.037 Uiso 1 1 calc R . .
C8 C 0.28735(17) 1.7080(6) 1.0967(7) 0.0382(14) Uani 1 1 d . . .
C9 C 0.30460(18) 1.7935(6) 0.9784(7) 0.0492(16) Uani 1 1 d . . .
H9A H 0.2838 1.8273 0.9000 0.059 Uiso 1 1 calc R . .
C10 C 0.35242(17) 1.8316(6) 0.9716(7) 0.0469(15) Uani 1 1 d . . .
H10A H 0.3634 1.8894 0.8894 0.056 Uiso 1 1 calc R . .
C11 C 0.38329(16) 1.7825(5) 1.0883(6) 0.0345(13) Uani 1 1 d . . .
C12 C 0.36676(18) 1.6930(6) 1.2069(7) 0.0457(14) Uani 1 1 d U . .
H12A H 0.3876 1.6586 1.2848 0.055 Uiso 1 1 calc R . .
C13 C 0.31911(17) 1.6547(6) 1.2095(7) 0.0423(14) Uani 1 1 d U . .
C14 C 0.43480(17) 1.8247(5) 1.0879(7) 0.0315(13) Uani 1 1 d . . .
C15 C 0.2060(3) 1.7832(9) 1.5038(8) 0.082(3) Uani 1 1 d . . .
H15A H 0.2248 1.8396 1.5753 0.122 Uiso 1 1 calc R . .
H15B H 0.2033 1.6911 1.5475 0.122 Uiso 1 1 calc R . .
H15C H 0.1748 1.8231 1.4928 0.122 Uiso 1 1 calc R . .
C16 C 0.3274(3) 1.5161(9) 1.4444(10) 0.119(3) Uani 1 1 d U . .
H16A H 0.3089 1.4529 1.5087 0.179 Uiso 1 1 calc R . .
H16B H 0.3369 1.5939 1.5096 0.179 Uiso 1 1 calc R . .
H16C H 0.3552 1.4694 1.4043 0.179 Uiso 1 1 calc R . .
C17 C 0.0835(3) 0.9918(8) 1.3048(9) 0.089(3) Uani 1 1 d . . .
H17A H 0.0884 1.0717 1.3724 0.134 Uiso 1 1 calc R . .
H17B H 0.1138 0.9548 1.2722 0.134 Uiso 1 1 calc R . .
H17C H 0.0661 0.9225 1.3641 0.134 Uiso 1 1 calc R . .
C18 C 0.0427(3) 0.9222(7) 1.0475(12) 0.102(3) Uani 1 1 d . . .
H18A H 0.0252 0.9630 0.9596 0.154 Uiso 1 1 calc R . .
H18B H 0.0231 0.8549 1.1014 0.154 Uiso 1 1 calc R . .
H18C H 0.0708 0.8776 1.0060 0.154 Uiso 1 1 calc R . .
C19 C 0.0452(2) 1.1605(7) 1.1300(8) 0.0536(17) Uani 1 1 d . . .
H19A H 0.0559 1.2293 1.2002 0.064 Uiso 1 1 calc R . .
C20 C -0.0603(2) 1.3419(6) 1.1874(8) 0.0411(15) Uani 1 1 d . . .
H20A H -0.0789 1.3169 1.2762 0.049 Uiso 1 1 calc R . .
N1 N 0.05667(19) 1.0315(5) 1.1633(6) 0.0519(14) Uani 1 1 d . . .


_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
Eu1 O2 2.314(4) 2_584 ?
Eu1 O1 2.338(3) . ?
Eu1 O4 2.340(3) 4_544 ?
Eu1 O3 2.355(3) 3_485 ?
Eu1 O7 2.389(4) . ?
Eu1 O8 2.434(4) 2_584 ?
Eu1 O9 2.528(4) . ?
Eu1 O8 2.579(4) . ?
Eu1 C20 2.892(6) . ?
Eu1 Eu1 4.4481(3) 2_585 ?
Eu1 Eu1 4.4481(3) 2_584 ?
O1 C1 1.249(6) . ?
O2 C1 1.252(7) . ?
O2 Eu1 2.314(4) 2_585 ?
O3 C14 1.252(6) . ?
O3 Eu1 2.355(3) 3_585 ?
O4 C14 1.259(6) . ?
O4 Eu1 2.340(3) 4 ?
O5 C6 1.353(6) . ?
O5 C15 1.414(7) . ?
O6 C13 1.357(6) . ?
O6 C16 1.375(8) . ?
O7 C19 1.212(6) . ?
O8 C20 1.265(6) . ?
O8 Eu1 2.434(4) 2_585 ?
O9 C20 1.229(7) . ?
C1 C2 1.497(6) . ?
C2 C3 1.388(7) . ?
C2 C7 1.396(7) . ?
C3 C4 1.386(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.410(7) . ?
C5 C8 1.488(6) . ?
C6 C7 1.389(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.366(7) . ?
C8 C13 1.387(7) . ?
C9 C10 1.391(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.379(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.384(7) . ?
C11 C14 1.501(6) . ?
C12 C13 1.386(7) . ?
C12 H12A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N1 1.441(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N1 1.474(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N1 1.311(7) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

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 Eu1 O1 155.13(14) 2_584 . ?
O2 Eu1 O4 81.78(13) 2_584 4_544 ?
O1 Eu1 O4 82.24(12) . 4_544 ?
O2 Eu1 O3 80.69(13) 2_584 3_485 ?
O1 Eu1 O3 102.71(13) . 3_485 ?
O4 Eu1 O3 145.93(13) 4_544 3_485 ?
O2 Eu1 O7 112.17(14) 2_584 . ?
O1 Eu1 O7 79.97(15) . . ?
O4 Eu1 O7 70.59(13) 4_544 . ?
O3 Eu1 O7 143.40(14) 3_485 . ?
O2 Eu1 O8 80.77(14) 2_584 2_584 ?
O1 Eu1 O8 76.47(12) . 2_584 ?
O4 Eu1 O8 73.46(12) 4_544 2_584 ?
O3 Eu1 O8 75.04(11) 3_485 2_584 ?
O7 Eu1 O8 139.11(13) . 2_584 ?
O2 Eu1 O9 74.07(14) 2_584 . ?
O1 Eu1 O9 130.78(14) . . ?
O4 Eu1 O9 122.45(13) 4_544 . ?
O3 Eu1 O9 79.93(13) 3_485 . ?
O7 Eu1 O9 71.80(14) . . ?
O8 Eu1 O9 146.93(12) 2_584 . ?
O2 Eu1 O8 121.43(13) 2_584 . ?
O1 Eu1 O8 82.49(12) . . ?
O4 Eu1 O8 141.47(12) 4_544 . ?
O3 Eu1 O8 72.20(11) 3_485 . ?
O7 Eu1 O8 72.02(13) . . ?
O8 Eu1 O8 135.68(7) 2_584 . ?
O9 Eu1 O8 50.99(12) . . ?
O2 Eu1 C20 97.50(16) 2_584 . ?
O1 Eu1 C20 107.20(15) . . ?
O4 Eu1 C20 136.65(15) 4_544 . ?
O3 Eu1 C20 74.74(14) 3_485 . ?
O7 Eu1 C20 69.76(16) . . ?
O8 Eu1 C20 149.60(14) 2_584 . ?
O9 Eu1 C20 25.07(14) . . ?
O8 Eu1 C20 25.93(13) . . ?
O2 Eu1 Eu1 135.29(10) 2_584 2_585 ?
O1 Eu1 Eu1 63.78(9) . 2_585 ?
O4 Eu1 Eu1 142.79(8) 4_544 2_585 ?
O3 Eu1 Eu1 62.18(9) 3_485 2_585 ?
O7 Eu1 Eu1 88.11(10) . 2_585 ?
O8 Eu1 Eu1 110.09(8) 2_584 2_585 ?
O9 Eu1 Eu1 75.59(10) . 2_585 ?
O8 Eu1 Eu1 26.61(7) . 2_585 ?
C20 Eu1 Eu1 51.16(12) . 2_585 ?
O2 Eu1 Eu1 55.60(10) 2_584 2_584 ?
O1 Eu1 Eu1 99.82(9) . 2_584 ?
O4 Eu1 Eu1 60.93(9) 4_544 2_584 ?
O3 Eu1 Eu1 85.09(9) 3_485 2_584 ?
O7 Eu1 Eu1 130.93(10) . 2_584 ?
O8 Eu1 Eu1 28.34(8) 2_584 2_584 ?
O9 Eu1 Eu1 129.17(9) . 2_584 ?
O8 Eu1 Eu1 157.05(7) . 2_584 ?
C20 Eu1 Eu1 149.11(12) . 2_584 ?
Eu1 Eu1 Eu1 136.215(10) 2_585 2_584 ?
C1 O1 Eu1 135.3(3) . . ?
C1 O2 Eu1 148.1(4) . 2_585 ?
C14 O3 Eu1 138.0(3) . 3_585 ?
C14 O4 Eu1 137.8(3) . 4 ?
C6 O5 C15 118.4(5) . . ?
C13 O6 C16 119.9(5) . . ?
C19 O7 Eu1 134.9(4) . . ?
C20 O8 Eu1 136.9(4) . 2_585 ?
C20 O8 Eu1 91.0(4) . . ?
Eu1 O8 Eu1 125.05(14) 2_585 . ?
C20 O9 Eu1 94.3(3) . . ?
O1 C1 O2 124.0(5) . . ?
O1 C1 C2 118.7(5) . . ?
O2 C1 C2 117.3(5) . . ?
C3 C2 C7 120.8(5) . . ?
C3 C2 C1 120.7(5) . . ?
C7 C2 C1 118.5(5) . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C5 C4 C3 122.2(5) . . ?
C5 C4 H4A 118.9 . . ?
C3 C4 H4A 118.9 . . ?
C4 C5 C6 118.1(5) . . ?
C4 C5 C8 121.4(5) . . ?
C6 C5 C8 120.5(5) . . ?
O5 C6 C7 123.6(5) . . ?
O5 C6 C5 115.5(5) . . ?
C7 C6 C5 120.8(5) . . ?
C6 C7 C2 119.2(5) . . ?
C6 C7 H7A 120.4 . . ?
C2 C7 H7A 120.4 . . ?
C9 C8 C13 118.4(5) . . ?
C9 C8 C5 120.4(5) . . ?
C13 C8 C5 121.1(5) . . ?
C8 C9 C10 121.9(5) . . ?
C8 C9 H9A 119.0 . . ?
C10 C9 H9A 119.0 . . ?
C11 C10 C9 119.1(5) . . ?
C11 C10 H10A 120.4 . . ?
C9 C10 H10A 120.4 . . ?
C10 C11 C12 119.8(4) . . ?
C10 C11 C14 120.7(5) . . ?
C12 C11 C14 119.5(5) . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
O6 C13 C12 123.8(5) . . ?
O6 C13 C8 115.5(4) . . ?
C12 C13 C8 120.7(5) . . ?
O3 C14 O4 124.0(5) . . ?
O3 C14 C11 118.4(5) . . ?
O4 C14 C11 117.6(5) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 N1 124.6(6) . . ?
O7 C19 H19A 117.7 . . ?
N1 C19 H19A 117.7 . . ?
O9 C20 O8 123.7(6) . . ?
O9 C20 Eu1 60.7(3) . . ?
O8 C20 Eu1 63.1(3) . . ?
O9 C20 H20A 118.1 . . ?
O8 C20 H20A 118.1 . . ?
Eu1 C20 H20A 178.7 . . ?
C19 N1 C17 123.3(6) . . ?
C19 N1 C18 118.3(6) . . ?
C17 N1 C18 118.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.067
####################################################################### 
# 
# 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_xh8
_database_code_depnum_ccdc_archive 'CCDC 976992'
_audit_update_record             
;
2013-12-13 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Gd N O9'
_chemical_formula_sum            'C20 H20 Gd N O9'
_chemical_formula_weight         575.62

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'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           'Orthorhombic '
_symmetry_space_group_name_H-M   'Pna21 '
_symmetry_space_group_name_Hall  'P 2c -2n  '

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

_cell_length_a                   28.017(3)
_cell_length_b                   9.6175(9)
_cell_length_c                   8.2586(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2225.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6091
_cell_measurement_theta_min      1.48
_cell_measurement_theta_max      26.85

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132
_exptl_absorpt_coefficient_mu    3.030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5825
_exptl_absorpt_correction_T_max  0.7936
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_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 Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15156
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3770
_reflns_number_gt                3422
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0101P)²+1.0714P] 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     SHELXL
_refine_ls_extinction_coef       0.00030(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.008(13)
_refine_ls_number_reflns         3770
_refine_ls_number_parameters     281
_refine_ls_number_restraints     44
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0431
_refine_ls_wR_factor_gt          0.0418
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.004
_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
Gd1 Gd -0.003747(5) 1.415120(16) 0.90705(9) 0.02618(7) Uani 1 1 d . . .
O1 O 0.07167(10) 1.4783(4) 0.9997(4) 0.0463(9) Uani 1 1 d . . .
O2 O 0.06324(11) 1.6118(4) 1.2161(4) 0.0412(8) Uani 1 1 d . . .
O3 O 0.45157(10) 1.8855(3) 0.9655(4) 0.0404(8) Uani 1 1 d . . .
O4 O 0.45926(10) 1.7963(3) 1.2122(4) 0.0368(8) Uani 1 1 d . . .
O5 O 0.22844(13) 1.7774(5) 1.3507(5) 0.0654(13) Uani 1 1 d . . .
O6 O 0.30071(12) 1.5620(4) 1.3162(5) 0.0719(13) Uani 1 1 d U . .
O7 O 0.02164(14) 1.1971(3) 1.0129(5) 0.0559(10) Uani 1 1 d . . .
O8 O -0.02231(10) 1.4120(3) 1.2116(4) 0.0334(7) Uani 1 1 d . . .
O9 O -0.07326(11) 1.3057(4) 1.0510(4) 0.0500(9) Uani 1 1 d . . .
C1 C 0.08779(15) 1.5577(4) 1.1076(6) 0.0327(11) Uani 1 1 d . . .
C2 C 0.13987(14) 1.5937(4) 1.1037(5) 0.0328(10) Uani 1 1 d . . .
C3 C 0.16793(15) 1.5563(5) 0.9714(6) 0.0425(12) Uani 1 1 d . . .
H3A H 0.1550 1.5068 0.8851 0.051 Uiso 1 1 calc R . .
C4 C 0.21589(15) 1.5951(5) 0.9716(6) 0.0460(13) Uani 1 1 d . . .
H4A H 0.2349 1.5710 0.8836 0.055 Uiso 1 1 calc R . .
C5 C 0.23621(15) 1.6686(5) 1.0993(6) 0.0383(11) Uani 1 1 d . . .
C6 C 0.20708(16) 1.7027(5) 1.2312(6) 0.0397(12) Uani 1 1 d . . .
C7 C 0.15902(14) 1.6663(5) 1.2326(6) 0.0348(11) Uani 1 1 d . . .
H7A H 0.1399 1.6907 1.3200 0.042 Uiso 1 1 calc R . .
C8 C 0.28766(15) 1.7074(5) 1.0944(6) 0.0432(11) Uani 1 1 d U . .
C9 C 0.30458(16) 1.7939(5) 0.9780(6) 0.0534(14) Uani 1 1 d . . .
H9A H 0.2837 1.8288 0.9004 0.064 Uiso 1 1 calc R . .
C10 C 0.35279(15) 1.8314(5) 0.9725(6) 0.0465(13) Uani 1 1 d . . .
H10A H 0.3639 1.8896 0.8907 0.056 Uiso 1 1 calc R . .
C11 C 0.38376(14) 1.7821(4) 1.0884(6) 0.0365(11) Uani 1 1 d . . .
C12 C 0.36694(16) 1.6925(5) 1.2064(7) 0.0467(11) Uani 1 1 d U . .
H12A H 0.3878 1.6576 1.2840 0.056 Uiso 1 1 calc R . .
C13 C 0.31923(16) 1.6545(5) 1.2100(7) 0.0461(11) Uani 1 1 d U . .
C14 C 0.43528(15) 1.8251(5) 1.0866(6) 0.0332(11) Uani 1 1 d . . .
C15 C 0.2058(2) 1.7836(8) 1.5034(8) 0.084(2) Uani 1 1 d . . .
H15A H 0.2245 1.8399 1.5756 0.126 Uiso 1 1 calc R . .
H15B H 0.2030 1.6915 1.5470 0.126 Uiso 1 1 calc R . .
H15C H 0.1746 1.8237 1.4915 0.126 Uiso 1 1 calc R . .
C16 C 0.3282(2) 1.5126(8) 1.4468(9) 0.104(2) Uani 1 1 d U . .
H16A H 0.3097 1.4477 1.5089 0.156 Uiso 1 1 calc R . .
H16B H 0.3374 1.5892 1.5144 0.156 Uiso 1 1 calc R . .
H16C H 0.3562 1.4671 1.4061 0.156 Uiso 1 1 calc R . .
C17 C 0.0837(3) 0.9918(7) 1.3026(8) 0.088(2) Uani 1 1 d . . .
H17A H 0.0886 1.0719 1.3701 0.132 Uiso 1 1 calc R . .
H17B H 0.1141 0.9555 1.2692 0.132 Uiso 1 1 calc R . .
H17C H 0.0667 0.9220 1.3623 0.132 Uiso 1 1 calc R . .
C18 C 0.0429(3) 0.9228(6) 1.0451(10) 0.099(2) Uani 1 1 d . . .
H18A H 0.0254 0.9639 0.9574 0.148 Uiso 1 1 calc R . .
H18B H 0.0233 0.8546 1.0981 0.148 Uiso 1 1 calc R . .
H18C H 0.0711 0.8790 1.0037 0.148 Uiso 1 1 calc R . .
C19 C 0.0449(2) 1.1607(5) 1.1288(7) 0.0544(14) Uani 1 1 d . . .
H19A H 0.0554 1.2292 1.1997 0.065 Uiso 1 1 calc R . .
C20 C -0.06019(17) 1.3435(5) 1.1869(7) 0.0403(13) Uani 1 1 d . . .
H20A H -0.0791 1.3205 1.2755 0.048 Uiso 1 1 calc R . .
N1 N 0.05635(16) 1.0312(4) 1.1615(6) 0.0529(12) Uani 1 1 d . . .


_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
Gd1 O2 2.309(3) 2_584 ?
Gd1 O1 2.328(3) . ?
Gd1 O4 2.334(3) 4_544 ?
Gd1 O3 2.341(3) 3_485 ?
Gd1 O7 2.381(3) . ?
Gd1 O8 2.430(3) 2_584 ?
Gd1 O9 2.512(3) . ?
Gd1 O8 2.568(3) . ?
Gd1 C20 2.884(5) . ?
O1 C1 1.257(5) . ?
O2 C1 1.244(6) . ?
O2 Gd1 2.309(3) 2_585 ?
O3 C14 1.243(5) . ?
O3 Gd1 2.341(3) 3_585 ?
O4 C14 1.267(5) . ?
O4 Gd1 2.334(3) 4 ?
O5 C6 1.360(5) . ?
O5 C15 1.413(7) . ?
O6 C13 1.354(6) . ?
O6 C16 1.408(7) . ?
O7 C19 1.209(6) . ?
O8 C20 1.265(5) . ?
O8 Gd1 2.430(3) 2_585 ?
O9 C20 1.236(6) . ?
C1 C2 1.500(6) . ?
C2 C7 1.381(6) . ?
C2 C3 1.393(6) . ?
C3 C4 1.394(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.392(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.400(7) . ?
C5 C8 1.490(6) . ?
C6 C7 1.391(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.357(6) . ?
C8 C13 1.397(7) . ?
C9 C10 1.399(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.377(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.383(6) . ?
C11 C14 1.502(6) . ?
C12 C13 1.386(6) . ?
C12 H12A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N1 1.446(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N1 1.467(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N1 1.314(6) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

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 Gd1 O1 155.36(12) 2_584 . ?
O2 Gd1 O4 81.94(11) 2_584 4_544 ?
O1 Gd1 O4 82.52(11) . 4_544 ?
O2 Gd1 O3 81.19(12) 2_584 3_485 ?
O1 Gd1 O3 101.75(11) . 3_485 ?
O4 Gd1 O3 146.00(11) 4_544 3_485 ?
O2 Gd1 O7 111.57(13) 2_584 . ?
O1 Gd1 O7 80.68(13) . . ?
O4 Gd1 O7 70.26(11) 4_544 . ?
O3 Gd1 O7 143.68(12) 3_485 . ?
O2 Gd1 O8 80.79(12) 2_584 2_584 ?
O1 Gd1 O8 76.53(11) . 2_584 ?
O4 Gd1 O8 73.54(11) 4_544 2_584 ?
O3 Gd1 O8 74.75(10) 3_485 2_584 ?
O7 Gd1 O8 139.20(12) . 2_584 ?
O2 Gd1 O9 73.53(12) 2_584 . ?
O1 Gd1 O9 131.10(12) . . ?
O4 Gd1 O9 122.34(11) 4_544 . ?
O3 Gd1 O9 80.27(11) 3_485 . ?
O7 Gd1 O9 71.88(13) . . ?
O8 Gd1 O9 146.49(11) 2_584 . ?
O2 Gd1 O8 121.41(11) 2_584 . ?
O1 Gd1 O8 82.24(10) . . ?
O4 Gd1 O8 141.02(10) 4_544 . ?
O3 Gd1 O8 72.50(10) 3_485 . ?
O7 Gd1 O8 71.97(11) . . ?
O8 Gd1 O8 136.01(6) 2_584 . ?
O9 Gd1 O8 51.31(10) . . ?
O2 Gd1 C20 97.17(13) 2_584 . ?
O1 Gd1 C20 107.24(13) . . ?
O4 Gd1 C20 136.74(13) 4_544 . ?
O3 Gd1 C20 74.76(12) 3_485 . ?
O7 Gd1 C20 70.07(13) . . ?
O8 Gd1 C20 149.39(12) 2_584 . ?
O9 Gd1 C20 25.30(12) . . ?
O8 Gd1 C20 26.02(11) . . ?
C1 O1 Gd1 135.9(3) . . ?
C1 O2 Gd1 147.6(3) . 2_585 ?
C14 O3 Gd1 138.1(3) . 3_585 ?
C14 O4 Gd1 137.8(3) . 4 ?
C6 O5 C15 118.2(4) . . ?
C13 O6 C16 120.6(4) . . ?
C19 O7 Gd1 135.0(4) . . ?
C20 O8 Gd1 135.6(3) . 2_585 ?
C20 O8 Gd1 91.1(3) . . ?
Gd1 O8 Gd1 125.57(11) 2_585 . ?
C20 O9 Gd1 94.4(3) . . ?
O2 C1 O1 124.5(4) . . ?
O2 C1 C2 117.2(4) . . ?
O1 C1 C2 118.3(4) . . ?
C7 C2 C3 121.0(4) . . ?
C7 C2 C1 118.5(4) . . ?
C3 C2 C1 120.4(4) . . ?
C2 C3 C4 118.3(4) . . ?
C2 C3 H3A 120.9 . . ?
C4 C3 H3A 120.9 . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 C8 120.2(4) . . ?
C6 C5 C8 121.8(4) . . ?
O5 C6 C7 123.6(5) . . ?
O5 C6 C5 115.6(4) . . ?
C7 C6 C5 120.8(4) . . ?
C2 C7 C6 119.8(4) . . ?
C2 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C9 C8 C13 119.1(4) . . ?
C9 C8 C5 120.7(4) . . ?
C13 C8 C5 120.2(4) . . ?
C8 C9 C10 121.3(4) . . ?
C8 C9 H9A 119.4 . . ?
C10 C9 H9A 119.4 . . ?
C11 C10 C9 119.8(4) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 119.3(4) . . ?
C10 C11 C14 120.3(4) . . ?
C12 C11 C14 120.4(4) . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
O6 C13 C12 123.8(4) . . ?
O6 C13 C8 116.1(4) . . ?
C12 C13 C8 120.0(5) . . ?
O3 C14 O4 124.5(4) . . ?
O3 C14 C11 119.3(4) . . ?
O4 C14 C11 116.2(4) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 N1 124.7(6) . . ?
O7 C19 H19A 117.7 . . ?
N1 C19 H19A 117.7 . . ?
O9 C20 O8 123.2(5) . . ?
O9 C20 Gd1 60.3(3) . . ?
O8 C20 Gd1 62.9(3) . . ?
O9 C20 H20A 118.4 . . ?
O8 C20 H20A 118.4 . . ?
Gd1 C20 H20A 178.5 . . ?
C19 N1 C17 122.9(5) . . ?
C19 N1 C18 118.4(5) . . ?
C17 N1 C18 118.6(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_xh7
_database_code_depnum_ccdc_archive 'CCDC 976993'
_audit_update_record             
;
2013-12-13 deposited with the CCDC.
2015-04-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Dy N O9'
_chemical_formula_sum            'C20 H20 Dy N O9'
_chemical_formula_weight         580.87

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           'Orthorhombic '
_symmetry_space_group_name_H-M   'Pna21 '
_symmetry_space_group_name_Hall  'P 2c -2n  '

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

_cell_length_a                   27.951(4)
_cell_length_b                   9.6124(13)
_cell_length_c                   8.1937(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2201.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3811
_cell_measurement_theta_min      1.48
_cell_measurement_theta_max      26.95

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    3.444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5179
_exptl_absorpt_correction_T_max  0.7702
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_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 Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15014
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3746
_reflns_number_gt                3164
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0176P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.00059(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(14)
_refine_ls_number_reflns         3746
_refine_ls_number_parameters     281
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0521
_refine_ls_wR_factor_gt          0.0494
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.007
_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 1.003767(6) -0.415197(19) 0.09288(12) 0.02445(8) Uani 1 1 d . . .
O1 O 0.92928(12) -0.4770(4) -0.0006(4) 0.0398(10) Uani 1 1 d . . .
O2 O 0.93764(14) -0.6128(4) -0.2171(5) 0.0378(11) Uani 1 1 d . . .
O3 O 0.54863(12) -0.8896(4) 0.0351(4) 0.0381(10) Uani 1 1 d . . .
O4 O 0.54097(12) -0.7986(4) -0.2145(5) 0.0348(10) Uani 1 1 d . . .
O5 O 0.77186(15) -0.7790(6) -0.3511(6) 0.0595(15) Uani 1 1 d . . .
O6 O 0.69966(15) -0.5618(5) -0.3154(6) 0.0674(16) Uani 1 1 d . . .
O7 O 0.97865(17) -0.1983(4) -0.0120(5) 0.0511(12) Uani 1 1 d . . .
O8 O 1.02158(12) -0.4122(4) -0.2121(5) 0.0312(9) Uani 1 1 d . . .
O9 O 1.07243(13) -0.3055(5) -0.0520(6) 0.0476(12) Uani 1 1 d . . .
C1 C 0.91317(19) -0.5590(6) -0.1080(7) 0.0307(14) Uani 1 1 d . . .
C2 C 0.86104(17) -0.5949(6) -0.1038(6) 0.0288(13) Uani 1 1 d . . .
C3 C 0.83282(18) -0.5543(6) 0.0299(7) 0.0390(15) Uani 1 1 d . . .
H3A H 0.8456 -0.5023 0.1152 0.047 Uiso 1 1 calc R . .
C4 C 0.78456(18) -0.5956(6) 0.0297(7) 0.0404(15) Uani 1 1 d . . .
H4A H 0.7656 -0.5733 0.1192 0.049 Uiso 1 1 calc R . .
C5 C 0.76428(18) -0.6680(6) -0.0983(7) 0.0358(14) Uani 1 1 d . . .
C6 C 0.7935(2) -0.7042(6) -0.2301(8) 0.0358(15) Uani 1 1 d . . .
C7 C 0.84133(17) -0.6663(6) -0.2317(7) 0.0311(13) Uani 1 1 d . . .
H7A H 0.8603 -0.6897 -0.3209 0.037 Uiso 1 1 calc R . .
C8 C 0.71251(18) -0.7062(6) -0.0920(7) 0.0375(13) Uani 1 1 d U . .
C9 C 0.69562(18) -0.7939(6) 0.0243(7) 0.0475(17) Uani 1 1 d . . .
H9A H 0.7167 -0.8295 0.1017 0.057 Uiso 1 1 calc R . .
C10 C 0.64743(18) -0.8320(6) 0.0308(7) 0.0445(17) Uani 1 1 d . . .
H10A H 0.6363 -0.8897 0.1137 0.053 Uiso 1 1 calc R . .
C11 C 0.61657(17) -0.7834(5) -0.0868(7) 0.0314(13) Uani 1 1 d . . .
C12 C 0.63333(18) -0.6938(6) -0.2063(8) 0.0416(13) Uani 1 1 d U . .
H12A H 0.6125 -0.6595 -0.2850 0.050 Uiso 1 1 calc R . .
C13 C 0.68070(19) -0.6557(6) -0.2084(8) 0.0428(13) Uani 1 1 d U . .
C14 C 0.56468(18) -0.8277(6) -0.0875(7) 0.0299(13) Uani 1 1 d . . .
C15 C 0.7938(3) -0.7840(10) -0.5067(9) 0.077(3) Uani 1 1 d . . .
H15A H 0.7750 -0.8406 -0.5786 0.116 Uiso 1 1 calc R . .
H15B H 0.8253 -0.8232 -0.4966 0.116 Uiso 1 1 calc R . .
H15C H 0.7962 -0.6915 -0.5503 0.116 Uiso 1 1 calc R . .
C16 C 0.6726(3) -0.5183(9) -0.4500(10) 0.103(2) Uani 1 1 d U . .
H16A H 0.6909 -0.4531 -0.5132 0.154 Uiso 1 1 calc R . .
H16B H 0.6437 -0.4746 -0.4126 0.154 Uiso 1 1 calc R . .
H16C H 0.6647 -0.5973 -0.5163 0.154 Uiso 1 1 calc R . .
C17 C 0.9169(3) 0.0054(8) -0.3029(9) 0.081(3) Uani 1 1 d . . .
H17A H 0.9121 -0.0751 -0.3703 0.121 Uiso 1 1 calc R . .
H17B H 0.9339 0.0749 -0.3636 0.121 Uiso 1 1 calc R . .
H17C H 0.8864 0.0419 -0.2697 0.121 Uiso 1 1 calc R . .
C18 C 0.9582(3) 0.0768(7) -0.0461(12) 0.093(3) Uani 1 1 d . . .
H18A H 0.9758 0.0359 0.0423 0.140 Uiso 1 1 calc R . .
H18B H 0.9301 0.1220 -0.0040 0.140 Uiso 1 1 calc R . .
H18C H 0.9779 0.1439 -0.1009 0.140 Uiso 1 1 calc R . .
C19 C 0.9553(2) -0.1626(7) -0.1276(9) 0.0500(17) Uani 1 1 d . . .
H19A H 0.9445 -0.2315 -0.1981 0.060 Uiso 1 1 calc R . .
C20 C 1.0593(2) -0.3442(6) -0.1866(8) 0.0340(15) Uani 1 1 d . . .
H20A H 1.0783 -0.3219 -0.2759 0.041 Uiso 1 1 calc R . .
N1 N 0.9439(2) -0.0325(5) -0.1620(7) 0.0502(15) Uani 1 1 d . . .


_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 2.276(4) 2_745 ?
Dy1 O1 2.297(3) . ?
Dy1 O4 2.304(4) 4_655 ?
Dy1 O3 2.306(3) 3_535 ?
Dy1 O7 2.362(4) . ?
Dy1 O8 2.410(4) 2_745 ?
Dy1 O9 2.491(4) . ?
Dy1 O8 2.548(4) . ?
Dy1 C20 2.849(6) . ?
O1 C1 1.264(6) . ?
O2 C1 1.239(7) . ?
O2 Dy1 2.276(4) 2_744 ?
O3 C14 1.251(6) . ?
O3 Dy1 2.306(3) 3_435 ?
O4 C14 1.265(6) . ?
O4 Dy1 2.304(4) 4_644 ?
O5 C6 1.365(6) . ?
O5 C15 1.416(7) . ?
O6 C13 1.365(7) . ?
O6 C16 1.401(8) . ?
O7 C19 1.201(7) . ?
O8 C20 1.258(6) . ?
O8 Dy1 2.410(4) 2_744 ?
O9 C20 1.221(7) . ?
C1 C2 1.498(7) . ?
C2 C7 1.369(7) . ?
C2 C3 1.405(7) . ?
C3 C4 1.406(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.398(8) . ?
C5 C8 1.494(7) . ?
C6 C7 1.387(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.357(7) . ?
C8 C13 1.392(8) . ?
C9 C10 1.397(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.374(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.386(7) . ?
C11 C14 1.512(7) . ?
C12 C13 1.374(7) . ?
C12 H12A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 N1 1.427(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N1 1.472(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N1 1.321(7) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?

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 155.66(15) 2_745 . ?
O2 Dy1 O4 82.20(14) 2_745 4_655 ?
O1 Dy1 O4 82.08(13) . 4_655 ?
O2 Dy1 O3 81.11(14) 2_745 3_535 ?
O1 Dy1 O3 102.36(13) . 3_535 ?
O4 Dy1 O3 146.25(14) 4_655 3_535 ?
O2 Dy1 O7 111.01(15) 2_745 . ?
O1 Dy1 O7 80.65(15) . . ?
O4 Dy1 O7 70.04(14) 4_655 . ?
O3 Dy1 O7 143.63(15) 3_535 . ?
O2 Dy1 O8 80.75(15) 2_745 2_745 ?
O1 Dy1 O8 77.09(13) . 2_745 ?
O4 Dy1 O8 73.80(13) 4_655 2_745 ?
O3 Dy1 O8 74.69(12) 3_535 2_745 ?
O7 Dy1 O8 139.60(14) . 2_745 ?
O2 Dy1 O9 73.83(16) 2_745 . ?
O1 Dy1 O9 130.48(15) . . ?
O4 Dy1 O9 122.59(14) 4_655 . ?
O3 Dy1 O9 80.08(14) 3_535 . ?
O7 Dy1 O9 71.45(15) . . ?
O8 Dy1 O9 146.50(13) 2_745 . ?
O2 Dy1 O8 121.95(14) 2_745 . ?
O1 Dy1 O8 81.54(12) . . ?
O4 Dy1 O8 140.55(13) 4_655 . ?
O3 Dy1 O8 72.62(12) 3_535 . ?
O7 Dy1 O8 72.02(13) . . ?
O8 Dy1 O8 135.68(8) 2_745 . ?
O9 Dy1 O8 51.50(13) . . ?
O2 Dy1 C20 97.46(16) 2_745 . ?
O1 Dy1 C20 106.71(16) . . ?
O4 Dy1 C20 136.84(16) 4_655 . ?
O3 Dy1 C20 74.56(15) 3_535 . ?
O7 Dy1 C20 69.99(16) . . ?
O8 Dy1 C20 149.10(15) 2_745 . ?
O9 Dy1 C20 25.31(15) . . ?
O8 Dy1 C20 26.19(14) . . ?
C1 O1 Dy1 135.8(3) . . ?
C1 O2 Dy1 147.3(4) . 2_744 ?
C14 O3 Dy1 138.4(3) . 3_435 ?
C14 O4 Dy1 137.8(4) . 4_644 ?
C6 O5 C15 118.6(5) . . ?
C13 O6 C16 119.6(5) . . ?
C19 O7 Dy1 134.5(5) . . ?
C20 O8 Dy1 135.6(4) . 2_744 ?
C20 O8 Dy1 90.4(4) . . ?
Dy1 O8 Dy1 125.81(14) 2_744 . ?
C20 O9 Dy1 94.0(4) . . ?
O2 C1 O1 124.5(5) . . ?
O2 C1 C2 117.2(5) . . ?
O1 C1 C2 118.3(5) . . ?
C7 C2 C3 120.7(5) . . ?
C7 C2 C1 119.3(5) . . ?
C3 C2 C1 120.0(5) . . ?
C2 C3 C4 117.3(5) . . ?
C2 C3 H3A 121.3 . . ?
C4 C3 H3A 121.3 . . ?
C5 C4 C3 122.5(5) . . ?
C5 C4 H4A 118.7 . . ?
C3 C4 H4A 118.7 . . ?
C4 C5 C6 118.2(5) . . ?
C4 C5 C8 119.7(5) . . ?
C6 C5 C8 122.1(5) . . ?
O5 C6 C7 123.9(6) . . ?
O5 C6 C5 115.8(5) . . ?
C7 C6 C5 120.3(5) . . ?
C2 C7 C6 120.9(5) . . ?
C2 C7 H7A 119.6 . . ?
C6 C7 H7A 119.6 . . ?
C9 C8 C13 118.4(5) . . ?
C9 C8 C5 121.0(5) . . ?
C13 C8 C5 120.6(5) . . ?
C8 C9 C10 121.7(5) . . ?
C8 C9 H9A 119.2 . . ?
C10 C9 H9A 119.2 . . ?
C11 C10 C9 119.3(5) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
C10 C11 C12 119.6(5) . . ?
C10 C11 C14 120.6(5) . . ?
C12 C11 C14 119.8(5) . . ?
C13 C12 C11 120.0(5) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
O6 C13 C12 124.0(5) . . ?
O6 C13 C8 115.0(5) . . ?
C12 C13 C8 120.9(6) . . ?
O3 C14 O4 125.3(5) . . ?
O3 C14 C11 118.3(5) . . ?
O4 C14 C11 116.4(5) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O7 C19 N1 124.8(7) . . ?
O7 C19 H19A 117.6 . . ?
N1 C19 H19A 117.6 . . ?
O9 C20 O8 124.1(6) . . ?
O9 C20 Dy1 60.7(3) . . ?
O8 C20 Dy1 63.4(3) . . ?
O9 C20 H20A 117.9 . . ?
O8 C20 H20A 117.9 . . ?
Dy1 C20 H20A 178.1 . . ?
C19 N1 C17 122.8(6) . . ?
C19 N1 C18 118.2(6) . . ?
C17 N1 C18 118.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.075
