# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1449725'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_audit_creation_date             2016-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H11 Eu O9, H2 O, C2 H3 N'
_chemical_formula_sum            'C17 H16 Eu N O10'
_chemical_formula_weight         546.27
_chemical_melting_point          ?
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'
Eu Eu -0.1578 3.6682 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.350(6)
_cell_length_b                   9.729(6)
_cell_length_c                   12.896(8)
_cell_angle_alpha                71.764(9)
_cell_angle_beta                 88.354(9)
_cell_angle_gamma                62.175(7)
_cell_volume                     975.7(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5075
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.537
_cell_measurement_theta_min      2.487
_shelx_estimated_absorpt_T_max   0.757
_shelx_estimated_absorpt_T_min   0.547
_exptl_absorpt_coefficient_mu    3.269
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0872 before and 0.0399 after correction.
The Ratio of minimum to maximum transmission is 0.7235.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4697
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.679
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3212
_reflns_number_total             3331
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.126
_refine_diff_density_min         -1.610
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0324
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0523P)²+2.6224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0929
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O8(H8A,H8B), O9(H9A,H9B), O10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.24174(2) 0.55247(2) 0.48158(2) 0.01319(12) Uani 1 1 d . . . . .
O1 O 0.1248(4) 0.4385(5) 0.6183(3) 0.0267(8) Uani 1 1 d . . . . .
O2 O -0.0616(4) 0.3664(5) 0.6777(3) 0.0262(8) Uani 1 1 d . . . . .
O3 O 0.4090(4) 0.2359(4) 0.7764(3) 0.0227(7) Uani 1 1 d . . . . .
O4 O 0.5175(4) 0.3676(4) 0.5805(3) 0.0210(7) Uani 1 1 d . . . . .
O5 O 0.7721(4) 0.1791(4) 0.6335(3) 0.0260(8) Uani 1 1 d . . . . .
O6 O 0.7282(4) -0.2962(4) 0.5397(3) 0.0212(7) Uani 1 1 d . . . . .
O7 O 0.5943(4) -0.4038(4) 0.6465(3) 0.0208(7) Uani 1 1 d . . . . .
O8 O -0.0250(4) 0.7841(4) 0.4902(3) 0.0279(8) Uani 1 1 d . . . . .
H8A H -0.0981 0.7601 0.5049 0.042 Uiso 1 1 d R . . . .
H8B H -0.0419 0.8684 0.4396 0.042 Uiso 1 1 d R . . . .
O9 O 0.2822(5) 0.6548(5) 0.6185(4) 0.0346(9) Uani 1 1 d . . . . .
H9A H 0.3765 0.6376 0.6262 0.052 Uiso 1 1 d R . . . .
H9B H 0.2234 0.7309 0.6404 0.052 Uiso 1 1 d R . . . .
O10 O 0.0823(6) 0.9121(6) 0.6920(4) 0.0516(13) Uani 1 1 d . . . . .
H10A H -0.0206 0.9711 0.6910 0.077 Uiso 1 1 d R . . . .
H10B H 0.1150 0.8883 0.7567 0.077 Uiso 1 1 d R . . . .
C1 C 0.0597(6) 0.3843(6) 0.6917(4) 0.0184(9) Uani 1 1 d . . . . .
C2 C 0.1270(6) 0.3338(6) 0.8101(4) 0.0181(9) Uani 1 1 d . . . . .
C3 C 0.2920(6) 0.2614(6) 0.8478(4) 0.0203(10) Uani 1 1 d . . . . .
C4 C 0.3454(7) 0.2167(7) 0.9575(5) 0.0325(13) Uani 1 1 d . . . . .
H4 H 0.4565 0.1671 0.9816 0.039 Uiso 1 1 calc R . . . .
C5 C 0.2362(8) 0.2447(8) 1.0314(5) 0.0372(14) Uani 1 1 d . . . . .
H5 H 0.2729 0.2165 1.1051 0.045 Uiso 1 1 calc R . . . .
C6 C 0.0747(7) 0.3134(8) 0.9971(5) 0.0355(13) Uani 1 1 d . . . . .
H6 H 0.0007 0.3304 1.0476 0.043 Uiso 1 1 calc R . . . .
C7 C 0.0193(7) 0.3584(7) 0.8868(4) 0.0279(11) Uani 1 1 d . . . . .
H7 H -0.0919 0.4059 0.8640 0.033 Uiso 1 1 calc R . . . .
C8 C 0.4544(5) 0.1077(5) 0.7385(4) 0.0142(9) Uani 1 1 d . . . . .
C9 C 0.5714(5) 0.0910(6) 0.6670(4) 0.0146(9) Uani 1 1 d . . . . .
C10 C 0.6325(6) -0.0417(6) 0.6294(4) 0.0174(9) Uani 1 1 d . . . . .
H10 H 0.7125 -0.0542 0.5832 0.021 Uiso 1 1 calc R . . . .
C11 C 0.5769(5) -0.1563(6) 0.6592(4) 0.0183(9) Uani 1 1 d . . . . .
C12 C 0.4607(6) -0.1381(6) 0.7295(4) 0.0213(10) Uani 1 1 d . . . . .
H12 H 0.4229 -0.2145 0.7506 0.026 Uiso 1 1 calc R . . . .
C13 C 0.3992(6) -0.0063(6) 0.7695(4) 0.0206(10) Uani 1 1 d . . . . .
H13 H 0.3209 0.0046 0.8170 0.025 Uiso 1 1 calc R . . . .
C14 C 0.6241(5) 0.2192(5) 0.6257(4) 0.0159(9) Uani 1 1 d . . . . .
C15 C 0.6358(5) -0.2929(6) 0.6138(4) 0.0174(9) Uani 1 1 d . . . . .
C16 C 0.765(2) 0.188(2) 0.8740(9) 0.134(7) Uani 1 1 d . . . . .
H16A H 0.6571 0.2723 0.8377 0.200 Uiso 1 1 calc GR . . . .
H16B H 0.7803 0.0826 0.8749 0.200 Uiso 1 1 calc GR . . . .
H16C H 0.8444 0.2108 0.8350 0.200 Uiso 1 1 calc GR . . . .
C17 C 0.7836(17) 0.184(2) 0.9868(8) 0.111(5) Uani 1 1 d . . . . .
N1 N 0.8029(15) 0.1711(19) 1.0751(7) 0.124(5) 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 Eu1 4.452(3) 2_666 ?
Eu1 O1 2.309(4) . ?
Eu1 O2 2.371(4) 2_566 ?
Eu1 O4 2.436(4) . ?
Eu1 O4 2.730(4) 2_666 ?
Eu1 O5 2.512(4) 2_666 ?
Eu1 O6 2.478(4) 2_656 ?
Eu1 O7 2.540(3) 2_656 ?
Eu1 O8 2.491(4) . ?
Eu1 O9 2.396(4) . ?
Eu1 H9A 2.7977 . ?
Eu1 C14 3.000(5) 2_666 ?
Eu1 C15 2.892(5) 2_656 ?
O1 C1 1.225(6) . ?
O2 Eu1 2.371(4) 2_566 ?
O2 C1 1.250(6) . ?
O3 C3 1.391(6) . ?
O3 C8 1.361(6) . ?
O4 Eu1 2.730(4) 2_666 ?
O4 C14 1.257(6) . ?
O5 Eu1 2.512(4) 2_666 ?
O5 C14 1.247(6) . ?
O6 Eu1 2.478(4) 2_656 ?
O6 C15 1.267(6) . ?
O7 Eu1 2.540(3) 2_656 ?
O7 C15 1.260(6) . ?
O8 H8A 0.8200 . ?
O8 H8B 0.8199 . ?
O9 H9A 0.8202 . ?
O9 H9B 0.8201 . ?
O10 H10A 0.8578 . ?
O10 H10B 0.8202 . ?
C1 C2 1.505(7) . ?
C2 C3 1.388(7) . ?
C2 C7 1.384(7) . ?
C3 C4 1.376(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.354(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(7) . ?
C8 C13 1.379(7) . ?
C9 C10 1.384(7) . ?
C9 C14 1.492(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(7) . ?
C11 C12 1.377(7) . ?
C11 C15 1.483(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.396(7) . ?
C13 H13 0.9300 . ?
C14 Eu1 3.000(5) 2_666 ?
C15 Eu1 2.892(5) 2_656 ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C17 1.457(15) . ?
C17 N1 1.117(13) . ?

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
Eu1 Eu1 H9A 54.7 2_666 . ?
O1 Eu1 Eu1 124.27(10) . 2_666 ?
O1 Eu1 O2 101.13(14) . 2_566 ?
O1 Eu1 O4 93.44(13) . . ?
O1 Eu1 O4 149.86(12) . 2_666 ?
O1 Eu1 O5 143.17(13) . 2_666 ?
O1 Eu1 O6 71.21(13) . 2_656 ?
O1 Eu1 O7 122.30(13) . 2_656 ?
O1 Eu1 O8 73.45(13) . . ?
O1 Eu1 O9 81.79(15) . . ?
O1 Eu1 H9A 92.4 . . ?
O1 Eu1 C14 154.35(13) . 2_666 ?
O1 Eu1 C15 96.82(14) . 2_656 ?
O2 Eu1 Eu1 130.60(9) 2_566 2_666 ?
O2 Eu1 O4 145.52(12) 2_566 . ?
O2 Eu1 O4 109.01(12) 2_566 2_666 ?
O2 Eu1 O5 77.79(13) 2_566 2_666 ?
O2 Eu1 O6 72.99(13) 2_566 2_656 ?
O2 Eu1 O7 71.78(13) 2_566 2_656 ?
O2 Eu1 O8 72.44(13) 2_566 . ?
O2 Eu1 O9 141.28(14) 2_566 . ?
O2 Eu1 H9A 149.6 2_566 . ?
O2 Eu1 C14 94.69(13) 2_566 2_666 ?
O2 Eu1 C15 70.19(13) 2_566 2_656 ?
O4 Eu1 Eu1 28.63(7) 2_666 2_666 ?
O4 Eu1 Eu1 32.47(8) . 2_666 ?
O4 Eu1 O4 61.10(13) . 2_666 ?
O4 Eu1 O5 108.17(11) . 2_666 ?
O4 Eu1 O6 82.65(12) . 2_656 ?
O4 Eu1 O7 73.99(12) . 2_656 ?
O4 Eu1 O8 142.02(12) . . ?
O4 Eu1 H9A 61.4 2_666 . ?
O4 Eu1 H9A 58.7 . . ?
O4 Eu1 C14 84.47(12) . 2_666 ?
O4 Eu1 C14 24.77(11) 2_666 2_666 ?
O4 Eu1 C15 92.99(12) 2_666 2_656 ?
O4 Eu1 C15 77.21(12) . 2_656 ?
O5 Eu1 Eu1 76.51(8) 2_666 2_666 ?
O5 Eu1 O4 48.80(10) 2_666 2_666 ?
O5 Eu1 O7 92.75(12) 2_666 2_656 ?
O5 Eu1 H9A 75.2 2_666 . ?
O5 Eu1 C14 24.14(12) 2_666 2_666 ?
O5 Eu1 C15 116.53(14) 2_666 2_656 ?
O6 Eu1 Eu1 102.02(8) 2_656 2_666 ?
O6 Eu1 O4 116.99(11) 2_656 2_666 ?
O6 Eu1 O5 139.36(13) 2_656 2_666 ?
O6 Eu1 O7 51.63(11) 2_656 2_656 ?
O6 Eu1 O8 123.57(12) 2_656 . ?
O6 Eu1 H9A 137.4 2_656 . ?
O6 Eu1 C14 133.38(12) 2_656 2_666 ?
O6 Eu1 C15 25.85(12) 2_656 2_656 ?
O7 Eu1 Eu1 68.15(8) 2_656 2_666 ?
O7 Eu1 O4 68.85(11) 2_656 2_666 ?
O7 Eu1 H9A 122.9 2_656 . ?
O7 Eu1 C14 81.75(12) 2_656 2_666 ?
O7 Eu1 C15 25.79(12) 2_656 2_656 ?
O8 Eu1 Eu1 134.28(9) . 2_666 ?
O8 Eu1 O4 115.79(12) . 2_666 ?
O8 Eu1 O5 71.19(12) . 2_666 ?
O8 Eu1 O7 143.13(12) . 2_656 ?
O8 Eu1 H9A 85.8 . . ?
O8 Eu1 C14 92.58(13) . 2_666 ?
O8 Eu1 C15 138.58(13) . 2_656 ?
O9 Eu1 Eu1 70.58(9) . 2_666 ?
O9 Eu1 O4 75.10(13) . 2_666 ?
O9 Eu1 O4 71.36(13) . . ?
O9 Eu1 O5 77.63(15) . 2_666 ?
O9 Eu1 O6 141.13(14) . 2_656 ?
O9 Eu1 O7 138.73(12) . 2_656 ?
O9 Eu1 O8 71.54(13) . . ?
O9 Eu1 H9A 15.9 . . ?
O9 Eu1 C14 73.31(14) . 2_666 ?
O9 Eu1 C15 148.37(13) . 2_656 ?
C14 Eu1 Eu1 52.44(9) 2_666 2_666 ?
C14 Eu1 H9A 64.7 2_666 . ?
C15 Eu1 Eu1 84.88(9) 2_656 2_666 ?
C15 Eu1 H9A 135.4 2_656 . ?
C15 Eu1 C14 107.54(13) 2_656 2_666 ?
C1 O1 Eu1 177.2(3) . . ?
C1 O2 Eu1 132.6(3) . 2_566 ?
C8 O3 C3 118.7(4) . . ?
Eu1 O4 Eu1 118.90(13) . 2_666 ?
C14 O4 Eu1 145.1(3) . . ?
C14 O4 Eu1 89.7(3) . 2_666 ?
C14 O5 Eu1 100.4(3) . 2_666 ?
C15 O6 Eu1 95.6(3) . 2_656 ?
C15 O7 Eu1 92.9(3) . 2_656 ?
Eu1 O8 H8A 115.0 . . ?
Eu1 O8 H8B 109.0 . . ?
H8A O8 H8B 120.6 . . ?
Eu1 O9 H9A 111.1 . . ?
Eu1 O9 H9B 134.5 . . ?
H9A O9 H9B 109.0 . . ?
H10A O10 H10B 100.1 . . ?
O1 C1 O2 125.5(5) . . ?
O1 C1 C2 119.2(4) . . ?
O2 C1 C2 115.3(4) . . ?
C3 C2 C1 123.8(4) . . ?
C7 C2 C1 118.6(4) . . ?
C7 C2 C3 117.6(5) . . ?
C2 C3 O3 121.8(5) . . ?
C4 C3 O3 117.4(5) . . ?
C4 C3 C2 120.8(5) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(5) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 121.0(5) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O3 C8 C9 115.2(4) . . ?
O3 C8 C13 124.9(4) . . ?
C13 C8 C9 119.8(4) . . ?
C8 C9 C14 120.8(4) . . ?
C10 C9 C8 119.3(4) . . ?
C10 C9 C14 119.8(4) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(4) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C15 121.3(4) . . ?
C12 C11 C10 118.7(4) . . ?
C12 C11 C15 120.0(4) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 120.0(4) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
O4 C14 Eu1 65.5(2) . 2_666 ?
O4 C14 C9 119.1(4) . . ?
O5 C14 Eu1 55.5(2) . 2_666 ?
O5 C14 O4 120.5(4) . . ?
O5 C14 C9 120.4(4) . . ?
C9 C14 Eu1 170.8(3) . 2_666 ?
O6 C15 Eu1 58.5(2) . 2_656 ?
O6 C15 C11 118.8(4) . . ?
O7 C15 Eu1 61.3(2) . 2_656 ?
O7 C15 O6 119.8(4) . . ?
O7 C15 C11 121.4(4) . . ?
C11 C15 Eu1 177.3(3) . 2_656 ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
N1 C17 C16 176(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O2 C1 O1 -8.0(7) 2_566 . . . ?
Eu1 O2 C1 C2 171.9(3) 2_566 . . . ?
Eu1 O4 C14 Eu1 146.8(5) . . . 2_666 ?
Eu1 O4 C14 O5 7.2(5) 2_666 . . . ?
Eu1 O4 C14 O5 154.0(4) . . . . ?
Eu1 O4 C14 C9 -24.3(8) . . . . ?
Eu1 O4 C14 C9 -171.1(4) 2_666 . . . ?
Eu1 O5 C14 O4 -8.0(5) 2_666 . . . ?
Eu1 O5 C14 C9 170.3(4) 2_666 . . . ?
Eu1 O6 C15 O7 -0.7(5) 2_656 . . . ?
Eu1 O6 C15 C11 -179.9(4) 2_656 . . . ?
Eu1 O7 C15 O6 0.7(4) 2_656 . . . ?
Eu1 O7 C15 C11 179.8(4) 2_656 . . . ?
O1 C1 C2 C3 -35.4(7) . . . . ?
O1 C1 C2 C7 145.5(5) . . . . ?
O2 C1 C2 C3 144.7(5) . . . . ?
O2 C1 C2 C7 -34.4(6) . . . . ?
O3 C3 C4 C5 177.3(5) . . . . ?
O3 C8 C9 C10 176.1(4) . . . . ?
O3 C8 C9 C14 -7.4(6) . . . . ?
O3 C8 C13 C12 -176.6(5) . . . . ?
C1 C2 C3 O3 2.7(8) . . . . ?
C1 C2 C3 C4 -179.4(5) . . . . ?
C1 C2 C7 C6 179.7(5) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . . ?
C3 O3 C8 C9 179.7(4) . . . . ?
C3 O3 C8 C13 -3.4(7) . . . . ?
C3 C2 C7 C6 0.5(8) . . . . ?
C3 C4 C5 C6 1.5(10) . . . . ?
C4 C5 C6 C7 -1.2(10) . . . . ?
C5 C6 C7 C2 0.2(9) . . . . ?
C7 C2 C3 O3 -178.1(5) . . . . ?
C7 C2 C3 C4 -0.2(8) . . . . ?
C8 O3 C3 C2 -77.0(6) . . . . ?
C8 O3 C3 C4 105.0(6) . . . . ?
C8 C9 C10 C11 1.6(7) . . . . ?
C8 C9 C14 O4 -53.1(6) . . . . ?
C8 C9 C14 O5 128.5(5) . . . . ?
C9 C8 C13 C12 0.2(7) . . . . ?
C9 C10 C11 C12 -1.3(7) . . . . ?
C9 C10 C11 C15 176.5(4) . . . . ?
C10 C9 C14 O4 123.3(5) . . . . ?
C10 C9 C14 O5 -55.0(6) . . . . ?
C10 C11 C12 C13 0.4(7) . . . . ?
C10 C11 C15 O6 -5.9(7) . . . . ?
C10 C11 C15 O7 175.0(4) . . . . ?
C11 C12 C13 C8 0.1(8) . . . . ?
C12 C11 C15 O6 171.9(4) . . . . ?
C12 C11 C15 O7 -7.2(7) . . . . ?
C13 C8 C9 C10 -1.0(7) . . . . ?
C13 C8 C9 C14 175.4(4) . . . . ?
C14 C9 C10 C11 -174.9(4) . . . . ?
C15 C11 C12 C13 -177.4(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1449726'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_audit_creation_date             2016-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H11 O9 Tb, H2 O, C2 H3 N'
_chemical_formula_sum            'C17 H16 N O10 Tb'
_chemical_formula_weight         553.23
_chemical_melting_point          ?
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'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3748(11)
_cell_length_b                   9.6792(11)
_cell_length_c                   12.9726(15)
_cell_angle_alpha                71.929(2)
_cell_angle_beta                 88.728(2)
_cell_angle_gamma                62.152(2)
_cell_volume                     978.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3888
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.422
_cell_measurement_theta_min      2.484
_shelx_estimated_absorpt_T_max   0.711
_shelx_estimated_absorpt_T_min   0.558
_exptl_absorpt_coefficient_mu    3.667
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0522 before and 0.0262 after correction.
The Ratio of minimum to maximum transmission is 0.8802.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4729
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.484
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3094
_reflns_number_total             3306
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3306
_refine_ls_number_restraints     198
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0242
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+1.7577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C14) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17,
 O1, O2, O3, O4, O5, O6, O7, O8, O9, O10, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Riding coordinates:
 O8(H8A,H8B), O9(H9A,H9B), O10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13)
4.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb -0.24030(2) 0.94665(2) 0.51835(2) 0.01391(8) Uani 1 1 d . . . . .
O1 O -0.1258(4) 1.0592(4) 0.3836(2) 0.0264(7) Uani 1 1 d . U . . .
O2 O 0.0602(4) 1.1337(4) 0.3251(2) 0.0258(7) Uani 1 1 d . U . . .
O3 O -0.4095(4) 1.2652(4) 0.2224(2) 0.0215(6) Uani 1 1 d . U . . .
O4 O -0.5127(4) 1.1315(3) 0.4211(2) 0.0213(6) Uani 1 1 d . U . . .
O5 O -0.7696(4) 1.3166(4) 0.3677(3) 0.0264(7) Uani 1 1 d . U . . .
O6 O -0.7276(4) 1.7977(4) 0.4603(3) 0.0225(7) Uani 1 1 d . U . . .
O7 O -0.5976(4) 1.9085(4) 0.3536(3) 0.0231(7) Uani 1 1 d . U . . .
O8 O 0.0242(4) 0.7157(4) 0.5102(3) 0.0258(7) Uani 1 1 d . U . . .
H8A H 0.0965 0.7407 0.4955 0.039 Uiso 1 1 d R . . . .
H8B H 0.0420 0.6308 0.5603 0.039 Uiso 1 1 d R . . . .
O9 O -0.2829(4) 0.8446(4) 0.3847(3) 0.0329(8) Uani 1 1 d . U . . .
H9A H -0.3779 0.8652 0.3747 0.049 Uiso 1 1 d R . . . .
H9B H -0.2250 0.7706 0.3607 0.049 Uiso 1 1 d R . . . .
O10 O 0.0819(5) 0.4111(5) 0.6919(3) 0.0492(10) Uani 1 1 d . U . . .
H10A H -0.0171 0.4581 0.6961 0.074 Uiso 1 1 d R . . . .
H10B H 0.1130 0.3907 0.7560 0.074 Uiso 1 1 d R . . . .
C1 C -0.0612(5) 1.1168(5) 0.3095(3) 0.0177(8) Uani 1 1 d . U . . .
C2 C -0.1269(5) 1.1665(5) 0.1917(3) 0.0187(8) Uani 1 1 d . U . . .
C3 C -0.2915(5) 1.2381(5) 0.1521(4) 0.0191(8) Uani 1 1 d . U . . .
C4 C -0.3441(6) 1.2823(6) 0.0429(4) 0.0300(10) Uani 1 1 d . U . . .
H4 H -0.4549 1.3318 0.0182 0.036 Uiso 1 1 calc R . . . .
C5 C -0.2350(7) 1.2540(7) -0.0295(4) 0.0358(12) Uani 1 1 d . U . . .
H5 H -0.2708 1.2821 -0.1030 0.043 Uiso 1 1 calc R . . . .
C6 C -0.0713(6) 1.1836(6) 0.0070(4) 0.0336(11) Uani 1 1 d . U . . .
H6 H 0.0031 1.1655 -0.0425 0.040 Uiso 1 1 calc R . . . .
C7 C -0.0164(6) 1.1397(6) 0.1162(4) 0.0281(10) Uani 1 1 d . U . . .
H7 H 0.0944 1.0921 0.1398 0.034 Uiso 1 1 calc R . . . .
C8 C -0.4564(5) 1.3951(5) 0.2611(3) 0.0155(8) Uani 1 1 d . U . . .
C9 C -0.5722(5) 1.4109(5) 0.3326(3) 0.0159(8) Uani 1 1 d . U . . .
C10 C -0.6332(5) 1.5424(5) 0.3709(3) 0.0175(8) Uani 1 1 d . U . . .
H10 H -0.7116 1.5537 0.4176 0.021 Uiso 1 1 calc R . . . .
C11 C -0.5784(5) 1.6590(5) 0.3402(3) 0.0182(8) Uani 1 1 d . U . . .
C12 C -0.4621(5) 1.6401(5) 0.2694(4) 0.0214(9) Uani 1 1 d . U . . .
H12 H -0.4244 1.7167 0.2488 0.026 Uiso 1 1 calc R . . . .
C13 C -0.4014(5) 1.5100(5) 0.2292(4) 0.0200(9) Uani 1 1 d . U . . .
H13 H -0.3247 1.4998 0.1814 0.024 Uiso 1 1 calc R . . . .
C14 C -0.6223(5) 1.2797(5) 0.3754(3) 0.0164(8) Uani 1 1 d . U . . .
C15 C -0.6384(5) 1.7962(5) 0.3874(3) 0.0178(8) Uani 1 1 d . U . . .
C16 C 0.2345(16) 0.3150(18) 0.1273(7) 0.134(5) Uani 1 1 d . U . . .
H16A H 0.3169 0.3441 0.1371 0.201 Uiso 1 1 calc GR . . . .
H16B H 0.2672 0.2043 0.1759 0.201 Uiso 1 1 calc GR . . . .
H16C H 0.1334 0.3913 0.1435 0.201 Uiso 1 1 calc GR . . . .
C17 C 0.2133(13) 0.3230(16) 0.0134(7) 0.104(4) Uani 1 1 d . U . . .
N1 N 0.2018(12) 0.3256(14) -0.0744(6) 0.117(4) Uani 1 1 d . U . . .


_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
Tb1 O1 2.285(3) . ?
Tb1 O2 2.351(3) 2_576 ?
Tb1 O4 2.782(3) 2_476 ?
Tb1 O4 2.406(3) . ?
Tb1 O5 2.477(3) 2_476 ?
Tb1 O6 2.452(3) 2_486 ?
Tb1 O7 2.525(3) 2_486 ?
Tb1 O8 2.473(3) . ?
Tb1 O9 2.367(3) . ?
Tb1 C14 3.008(4) 2_476 ?
Tb1 C15 2.858(4) 2_486 ?
O1 C1 1.250(5) . ?
O2 Tb1 2.351(3) 2_576 ?
O2 C1 1.251(5) . ?
O3 C3 1.398(5) . ?
O3 C8 1.376(5) . ?
O4 Tb1 2.782(3) 2_476 ?
O4 C14 1.260(5) . ?
O5 Tb1 2.477(3) 2_476 ?
O5 C14 1.253(5) . ?
O6 Tb1 2.452(3) 2_486 ?
O6 C15 1.248(5) . ?
O7 Tb1 2.525(3) 2_486 ?
O7 C15 1.267(5) . ?
O8 H8A 0.8201 . ?
O8 H8B 0.8196 . ?
O9 H9A 0.8202 . ?
O9 H9B 0.8202 . ?
O10 H10A 0.8306 . ?
O10 H10B 0.8197 . ?
C1 C2 1.502(6) . ?
C2 C3 1.393(6) . ?
C2 C7 1.400(6) . ?
C3 C4 1.376(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(6) . ?
C8 C13 1.383(6) . ?
C9 C10 1.377(6) . ?
C9 C14 1.500(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(6) . ?
C11 C12 1.392(6) . ?
C11 C15 1.498(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(6) . ?
C13 H13 0.9300 . ?
C14 Tb1 3.008(4) 2_476 ?
C15 Tb1 2.858(4) 2_486 ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C17 1.469(12) . ?
C17 N1 1.137(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
O1 Tb1 O2 101.00(11) . 2_576 ?
O1 Tb1 O4 149.13(10) . 2_476 ?
O1 Tb1 O4 93.30(11) . . ?
O1 Tb1 O5 143.98(11) . 2_476 ?
O1 Tb1 O6 71.84(10) . 2_486 ?
O1 Tb1 O7 123.42(10) . 2_486 ?
O1 Tb1 O8 73.24(11) . . ?
O1 Tb1 O9 82.03(12) . . ?
O1 Tb1 C14 154.38(11) . 2_476 ?
O1 Tb1 C15 97.39(12) . 2_486 ?
O2 Tb1 O4 109.86(10) 2_576 2_476 ?
O2 Tb1 O4 145.44(11) 2_576 . ?
O2 Tb1 O5 78.15(11) 2_576 2_476 ?
O2 Tb1 O6 73.07(11) 2_576 2_486 ?
O2 Tb1 O7 71.83(11) 2_576 2_486 ?
O2 Tb1 O8 72.26(11) 2_576 . ?
O2 Tb1 O9 141.39(11) 2_576 . ?
O2 Tb1 C14 95.28(11) 2_576 2_476 ?
O2 Tb1 C15 70.23(11) 2_576 2_486 ?
O4 Tb1 O4 60.57(11) . 2_476 ?
O4 Tb1 O5 107.71(10) . 2_476 ?
O4 Tb1 O6 81.99(10) . 2_486 ?
O4 Tb1 O7 74.01(10) . 2_486 ?
O4 Tb1 O8 142.30(10) . . ?
O4 Tb1 C14 84.07(10) . 2_476 ?
O4 Tb1 C14 24.75(10) 2_476 2_476 ?
O4 Tb1 C15 92.47(10) 2_476 2_486 ?
O4 Tb1 C15 76.87(11) . 2_486 ?
O5 Tb1 O4 48.62(9) 2_476 2_476 ?
O5 Tb1 O7 90.95(10) 2_476 2_486 ?
O5 Tb1 C14 23.99(10) 2_476 2_476 ?
O5 Tb1 C15 115.42(11) 2_476 2_486 ?
O6 Tb1 O4 116.16(9) 2_486 2_476 ?
O6 Tb1 O5 138.53(10) 2_486 2_476 ?
O6 Tb1 O7 52.07(9) 2_486 2_486 ?
O6 Tb1 O8 123.92(10) 2_486 . ?
O6 Tb1 C14 132.47(10) 2_486 2_476 ?
O6 Tb1 C15 25.76(11) 2_486 2_486 ?
O7 Tb1 O4 68.05(9) 2_486 2_476 ?
O7 Tb1 C14 80.41(10) 2_486 2_476 ?
O7 Tb1 C15 26.32(11) 2_486 2_486 ?
O8 Tb1 O4 116.45(9) . 2_476 ?
O8 Tb1 O5 72.31(10) . 2_476 ?
O8 Tb1 O7 142.76(11) . 2_486 ?
O8 Tb1 C14 93.39(10) . 2_476 ?
O8 Tb1 C15 138.63(11) . 2_486 ?
O9 Tb1 O4 74.42(10) . 2_476 ?
O9 Tb1 O4 71.38(10) . . ?
O9 Tb1 O5 77.68(12) . 2_476 ?
O9 Tb1 O6 141.34(11) . 2_486 ?
O9 Tb1 O7 137.92(10) . 2_486 ?
O9 Tb1 O8 71.94(11) . . ?
O9 Tb1 C14 72.96(12) . 2_476 ?
O9 Tb1 C15 148.13(11) . 2_486 ?
C15 Tb1 C14 106.72(11) 2_486 2_476 ?
C1 O1 Tb1 178.3(3) . . ?
C1 O2 Tb1 133.7(3) . 2_576 ?
C8 O3 C3 119.5(3) . . ?
Tb1 O4 Tb1 119.43(11) . 2_476 ?
C14 O4 Tb1 146.9(3) . . ?
C14 O4 Tb1 87.7(2) . 2_476 ?
C14 O5 Tb1 102.5(2) . 2_476 ?
C15 O6 Tb1 95.6(2) . 2_486 ?
C15 O7 Tb1 91.6(2) . 2_486 ?
Tb1 O8 H8A 114.6 . . ?
Tb1 O8 H8B 109.2 . . ?
H8A O8 H8B 120.9 . . ?
Tb1 O9 H9A 112.0 . . ?
Tb1 O9 H9B 135.2 . . ?
H9A O9 H9B 109.4 . . ?
H10A O10 H10B 95.9 . . ?
O1 C1 O2 124.8(4) . . ?
O1 C1 C2 119.5(4) . . ?
O2 C1 C2 115.6(4) . . ?
C3 C2 C1 124.2(4) . . ?
C3 C2 C7 117.5(4) . . ?
C7 C2 C1 118.2(4) . . ?
C2 C3 O3 121.2(4) . . ?
C4 C3 O3 117.4(4) . . ?
C4 C3 C2 121.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.7(4) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(5) . . ?
C6 C7 H7 119.8 . . ?
O3 C8 C9 115.6(3) . . ?
O3 C8 C13 123.8(4) . . ?
C13 C8 C9 120.5(4) . . ?
C8 C9 C14 121.0(4) . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 C14 119.0(4) . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C15 120.1(4) . . ?
C12 C11 C10 118.6(4) . . ?
C12 C11 C15 121.2(4) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 H13 120.5 . . ?
C12 C13 C8 119.1(4) . . ?
C12 C13 H13 120.5 . . ?
O4 C14 Tb1 67.5(2) . 2_476 ?
O4 C14 C9 118.4(4) . . ?
O5 C14 Tb1 53.5(2) . 2_476 ?
O5 C14 O4 120.6(4) . . ?
O5 C14 C9 121.0(4) . . ?
C9 C14 Tb1 170.4(3) . 2_476 ?
O6 C15 Tb1 58.6(2) . 2_486 ?
O6 C15 O7 120.7(4) . . ?
O6 C15 C11 119.4(4) . . ?
O7 C15 Tb1 62.0(2) . 2_486 ?
O7 C15 C11 120.0(4) . . ?
C11 C15 Tb1 178.0(3) . 2_486 ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
N1 C17 C16 177.9(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Tb1 O2 C1 O1 6.9(7) 2_576 . . . ?
Tb1 O2 C1 C2 -171.3(3) 2_576 . . . ?
Tb1 O4 C14 Tb1 -147.1(5) . . . 2_476 ?
Tb1 O4 C14 O5 -7.2(4) 2_476 . . . ?
Tb1 O4 C14 O5 -154.3(4) . . . . ?
Tb1 O4 C14 C9 24.5(7) . . . . ?
Tb1 O4 C14 C9 171.6(3) 2_476 . . . ?
Tb1 O5 C14 O4 8.3(4) 2_476 . . . ?
Tb1 O5 C14 C9 -170.5(3) 2_476 . . . ?
Tb1 O6 C15 O7 0.7(4) 2_486 . . . ?
Tb1 O6 C15 C11 -179.8(3) 2_486 . . . ?
Tb1 O7 C15 O6 -0.7(4) 2_486 . . . ?
Tb1 O7 C15 C11 179.8(3) 2_486 . . . ?
O1 C1 C2 C3 36.0(6) . . . . ?
O1 C1 C2 C7 -144.1(4) . . . . ?
O2 C1 C2 C3 -145.7(4) . . . . ?
O2 C1 C2 C7 34.2(6) . . . . ?
O3 C3 C4 C5 -177.8(4) . . . . ?
O3 C8 C9 C10 -176.4(4) . . . . ?
O3 C8 C9 C14 8.2(6) . . . . ?
O3 C8 C13 C12 177.0(4) . . . . ?
C1 C2 C3 O3 -1.7(6) . . . . ?
C1 C2 C3 C4 179.4(4) . . . . ?
C1 C2 C7 C6 -179.9(4) . . . . ?
C2 C3 C4 C5 1.2(7) . . . . ?
C3 O3 C8 C9 -178.7(4) . . . . ?
C3 O3 C8 C13 4.4(6) . . . . ?
C3 C2 C7 C6 0.0(7) . . . . ?
C3 C4 C5 C6 -1.3(8) . . . . ?
C4 C5 C6 C7 0.7(8) . . . . ?
C5 C6 C7 C2 -0.1(8) . . . . ?
C7 C2 C3 O3 178.3(4) . . . . ?
C7 C2 C3 C4 -0.5(6) . . . . ?
C8 O3 C3 C2 75.8(5) . . . . ?
C8 O3 C3 C4 -105.3(5) . . . . ?
C8 C9 C10 C11 -1.0(6) . . . . ?
C8 C9 C14 O4 53.3(5) . . . . ?
C8 C9 C14 O5 -127.9(4) . . . . ?
C9 C8 C13 C12 0.3(6) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C9 C10 C11 C15 -176.5(4) . . . . ?
C10 C9 C14 O4 -122.1(4) . . . . ?
C10 C9 C14 O5 56.7(6) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C10 C11 C15 O6 5.5(6) . . . . ?
C10 C11 C15 O7 -175.0(4) . . . . ?
C11 C12 C13 C8 -0.7(7) . . . . ?
C12 C11 C15 O6 -171.5(4) . . . . ?
C12 C11 C15 O7 8.0(6) . . . . ?
C13 C8 C9 C10 0.6(6) . . . . ?
C13 C8 C9 C14 -174.8(4) . . . . ?
C14 C9 C10 C11 174.4(4) . . . . ?
C15 C11 C12 C13 177.3(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1449727'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_audit_creation_date             2016-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H11 Dy O9, H2 O, C2 H3 N'
_chemical_formula_sum            'C17 H16 Dy N O10'
_chemical_formula_weight         556.81
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.365(4)
_cell_length_b                   9.648(4)
_cell_length_c                   12.980(5)
_cell_angle_alpha                72.191(6)
_cell_angle_beta                 89.080(5)
_cell_angle_gamma                62.247(5)
_cell_volume                     977.0(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4077
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.392
_cell_measurement_theta_min      2.550
_shelx_estimated_absorpt_T_max   0.675
_shelx_estimated_absorpt_T_min   0.496
_exptl_absorpt_coefficient_mu    3.879
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0744 before and 0.0354 after correction.
The Ratio of minimum to maximum transmission is 0.8013.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4783
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.486
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3095
_reflns_number_total             3302
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        APEX2
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         2.240
_refine_diff_density_min         -1.191
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+3.2830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
3. Rigid body (RIGU) restrains
 C16, C17, N1, C9, O5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Riding coordinates:
 O8(H8A,H8B), O9(H9A,H9B), O10(H10A,H10B), C16(H16A,H16B,H16C)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.73918(3) 0.55359(3) 0.48192(2) 0.01595(11) Uani 1 1 d . . . . .
O1 O 0.6262(5) 0.4419(5) 0.6168(3) 0.0286(9) Uani 1 1 d . . . . .
O2 O 0.4404(5) 0.3665(5) 0.6730(3) 0.0276(9) Uani 1 1 d . . . . .
O3 O 0.9102(5) 0.2340(5) 0.7783(3) 0.0237(8) Uani 1 1 d . . . . .
O4 O 1.0094(5) 0.3694(5) 0.5778(3) 0.0253(9) Uani 1 1 d . . . . .
O5 O 1.2679(5) 0.1859(5) 0.6305(3) 0.0275(9) Uani 1 1 d . U . . .
O6 O 1.2292(5) -0.2980(5) 0.5387(3) 0.0258(9) Uani 1 1 d . . . . .
O7 O 1.0989(5) -0.4100(5) 0.6461(3) 0.0235(8) Uani 1 1 d . . . . .
O8 O 0.4768(5) 0.7846(5) 0.4910(4) 0.0292(9) Uani 1 1 d . . . . .
H8A H 0.4038 0.7605 0.5046 0.044 Uiso 1 1 d R . . . .
H8B H 0.4613 0.8678 0.4399 0.044 Uiso 1 1 d R . . . .
O9 O 0.7828(5) 0.6550(6) 0.6154(4) 0.0364(11) Uani 1 1 d . . . . .
H9A H 0.8771 0.6370 0.6244 0.055 Uiso 1 1 d R . . . .
H9B H 0.7240 0.7313 0.6373 0.055 Uiso 1 1 d R . . . .
O10 O 0.5806(7) 0.9138(7) 0.6914(5) 0.0528(14) Uani 1 1 d . . . . .
H10A H 0.4770 0.9635 0.6983 0.079 Uiso 1 1 d R . . . .
H10B H 0.6109 0.8914 0.7562 0.079 Uiso 1 1 d R . . . .
C1 C 0.5613(7) 0.3854(7) 0.6900(5) 0.0200(11) Uani 1 1 d . . . . .
C2 C 0.6249(7) 0.3351(7) 0.8081(5) 0.0227(12) Uani 1 1 d . . . . .
C3 C 0.5187(8) 0.3608(8) 0.8827(5) 0.0310(14) Uani 1 1 d . . . . .
H3 H 0.4078 0.4103 0.8579 0.037 Uiso 1 1 calc R . . . .
C4 C 0.5677(9) 0.3172(9) 0.9922(5) 0.0359(15) Uani 1 1 d . . . . .
H4 H 0.4920 0.3346 1.0406 0.043 Uiso 1 1 calc R . . . .
C5 C 0.7347(9) 0.2458(10) 1.0296(6) 0.0401(16) Uani 1 1 d . . . . .
H5 H 0.7705 0.2185 1.1031 0.048 Uiso 1 1 calc R . . . .
C6 C 0.8448(8) 0.2165(9) 0.9577(5) 0.0330(14) Uani 1 1 d . . . . .
H6 H 0.9556 0.1660 0.9831 0.040 Uiso 1 1 calc R . . . .
C7 C 0.7929(7) 0.2613(7) 0.8477(5) 0.0218(12) Uani 1 1 d . . . . .
C8 C 0.9577(6) 0.1047(7) 0.7388(4) 0.0170(11) Uani 1 1 d . . . . .
C9 C 1.0730(6) 0.0902(7) 0.6673(4) 0.0175(11) Uani 1 1 d . U . . .
C10 C 1.1333(6) -0.0430(7) 0.6290(5) 0.0189(11) Uani 1 1 d . . . . .
H10 H 1.2112 -0.0543 0.5822 0.023 Uiso 1 1 calc R . . . .
C11 C 1.0794(6) -0.1602(7) 0.6592(5) 0.0206(11) Uani 1 1 d . . . . .
C12 C 0.9643(7) -0.1429(7) 0.7304(5) 0.0220(12) Uani 1 1 d . . . . .
H12 H 0.9280 -0.2208 0.7518 0.026 Uiso 1 1 calc R . . . .
C13 C 0.9030(7) -0.0109(7) 0.7700(5) 0.0225(12) Uani 1 1 d . . . . .
H13 H 0.8256 -0.0001 0.8172 0.027 Uiso 1 1 calc R . . . .
C14 C 1.1202(6) 0.2222(7) 0.6255(4) 0.0172(11) Uani 1 1 d . . . . .
C15 C 1.1388(6) -0.2960(7) 0.6120(4) 0.0190(11) Uani 1 1 d . . . . .
C16 C 0.265(2) 0.190(2) 0.8735(9) 0.123(6) Uani 1 1 d . U . . .
H16A H 0.1525 0.2706 0.8455 0.184 Uiso 1 1 d R . . . .
H16B H 0.2844 0.0838 0.8714 0.184 Uiso 1 1 d R . . . .
H16C H 0.3336 0.2238 0.8295 0.184 Uiso 1 1 d R . . . .
C17 C 0.2851(18) 0.178(2) 0.9862(9) 0.110(5) Uani 1 1 d . U . . .
N1 N 0.3056(15) 0.1680(19) 1.0749(8) 0.117(5) Uani 1 1 d . U . . .


_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 O1 2.279(4) . ?
Dy1 O2 2.328(4) 2_666 ?
Dy1 O4 2.813(4) 2_766 ?
Dy1 O4 2.381(4) . ?
Dy1 O5 2.461(4) 2_766 ?
Dy1 O6 2.441(4) 2_756 ?
Dy1 O7 2.521(4) 2_756 ?
Dy1 O8 2.464(4) . ?
Dy1 O9 2.357(4) . ?
Dy1 C14 3.017(5) 2_766 ?
Dy1 C15 2.852(5) 2_756 ?
O1 C1 1.242(7) . ?
O2 Dy1 2.328(4) 2_666 ?
O2 C1 1.260(7) . ?
O3 C7 1.390(7) . ?
O3 C8 1.373(7) . ?
O4 Dy1 2.813(4) 2_766 ?
O4 C14 1.260(7) . ?
O5 Dy1 2.461(4) 2_766 ?
O5 C14 1.256(7) . ?
O6 Dy1 2.441(4) 2_756 ?
O6 C15 1.261(7) . ?
O7 Dy1 2.521(4) 2_756 ?
O7 C15 1.274(7) . ?
O8 H8A 0.8199 . ?
O8 H8B 0.8200 . ?
O9 H9A 0.8201 . ?
O9 H9B 0.8198 . ?
O10 H10A 0.8770 . ?
O10 H10B 0.8198 . ?
C1 C2 1.498(8) . ?
C2 C3 1.369(9) . ?
C2 C7 1.416(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.405(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(10) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(9) . ?
C8 C9 1.399(8) . ?
C8 C13 1.385(8) . ?
C9 C10 1.387(8) . ?
C9 C14 1.485(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(8) . ?
C11 C12 1.394(8) . ?
C11 C15 1.483(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.387(8) . ?
C13 H13 0.9300 . ?
C14 Dy1 3.017(5) 2_766 ?
C15 Dy1 2.852(5) 2_756 ?
C16 H16A 0.9602 . ?
C16 H16B 0.9601 . ?
C16 H16C 0.9598 . ?
C16 C17 1.440(16) . ?
C17 N1 1.137(14) . ?

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
O1 Dy1 O2 101.35(15) . 2_666 ?
O1 Dy1 O4 148.46(14) . 2_766 ?
O1 Dy1 O4 93.07(15) . . ?
O1 Dy1 O5 144.20(15) . 2_766 ?
O1 Dy1 O6 71.98(15) . 2_756 ?
O1 Dy1 O7 124.11(14) . 2_756 ?
O1 Dy1 O8 73.21(15) . . ?
O1 Dy1 O9 81.50(16) . . ?
O1 Dy1 C14 154.63(15) . 2_766 ?
O1 Dy1 C15 97.87(16) . 2_756 ?
O2 Dy1 O4 110.19(13) 2_666 2_766 ?
O2 Dy1 O4 145.30(15) 2_666 . ?
O2 Dy1 O5 78.50(14) 2_666 2_766 ?
O2 Dy1 O6 73.35(15) 2_666 2_756 ?
O2 Dy1 O7 72.03(14) 2_666 2_756 ?
O2 Dy1 O8 72.55(15) 2_666 . ?
O2 Dy1 O9 141.41(16) 2_666 . ?
O2 Dy1 C14 95.14(14) 2_666 2_766 ?
O2 Dy1 C15 70.58(15) 2_666 2_756 ?
O4 Dy1 O4 60.29(15) . 2_766 ?
O4 Dy1 O5 107.32(14) . 2_766 ?
O4 Dy1 O6 81.60(14) . 2_756 ?
O4 Dy1 O7 73.73(14) . 2_756 ?
O4 Dy1 O8 142.15(14) . . ?
O4 Dy1 C14 83.90(14) . 2_766 ?
O4 Dy1 C14 24.64(13) 2_766 2_766 ?
O4 Dy1 C15 92.06(13) 2_766 2_756 ?
O4 Dy1 C15 76.32(14) . 2_756 ?
O5 Dy1 O4 48.43(12) 2_766 2_766 ?
O5 Dy1 O7 90.31(13) 2_766 2_756 ?
O5 Dy1 O8 72.71(14) 2_766 . ?
O5 Dy1 C14 23.84(14) 2_766 2_766 ?
O5 Dy1 C15 115.15(15) 2_766 2_756 ?
O6 Dy1 O4 116.05(12) 2_756 2_766 ?
O6 Dy1 O5 138.72(14) 2_756 2_766 ?
O6 Dy1 O7 52.65(13) 2_756 2_756 ?
O6 Dy1 O8 124.28(14) 2_756 . ?
O6 Dy1 C14 131.90(14) 2_756 2_766 ?
O6 Dy1 C15 26.13(15) 2_756 2_756 ?
O7 Dy1 O4 67.60(12) 2_756 2_766 ?
O7 Dy1 C14 79.27(13) 2_756 2_766 ?
O7 Dy1 C15 26.53(14) 2_756 2_756 ?
O8 Dy1 O4 116.50(13) . 2_766 ?
O8 Dy1 O7 143.08(14) . 2_756 ?
O8 Dy1 C14 93.86(14) . 2_766 ?
O8 Dy1 C15 139.36(14) . 2_756 ?
O9 Dy1 O4 71.56(15) . . ?
O9 Dy1 O4 74.43(14) . 2_766 ?
O9 Dy1 O5 77.71(16) . 2_766 ?
O9 Dy1 O6 140.95(16) . 2_756 ?
O9 Dy1 O7 137.63(14) . 2_756 ?
O9 Dy1 O8 71.59(15) . . ?
O9 Dy1 C14 73.63(16) . 2_766 ?
O9 Dy1 C15 147.77(15) . 2_756 ?
C15 Dy1 C14 105.79(15) 2_756 2_766 ?
C1 O1 Dy1 178.2(4) . . ?
C1 O2 Dy1 134.2(4) . 2_666 ?
C8 O3 C7 120.0(4) . . ?
Dy1 O4 Dy1 119.71(15) . 2_766 ?
C14 O4 Dy1 148.5(3) . . ?
C14 O4 Dy1 86.8(3) . 2_766 ?
C14 O5 Dy1 103.8(3) . 2_766 ?
C15 O6 Dy1 95.4(3) . 2_756 ?
C15 O7 Dy1 91.4(3) . 2_756 ?
Dy1 O8 H8A 114.6 . . ?
Dy1 O8 H8B 107.3 . . ?
H8A O8 H8B 121.0 . . ?
Dy1 O9 H9A 112.3 . . ?
Dy1 O9 H9B 133.9 . . ?
H9A O9 H9B 109.0 . . ?
H10A O10 H10B 93.1 . . ?
O1 C1 O2 124.5(5) . . ?
O1 C1 C2 120.4(5) . . ?
O2 C1 C2 115.1(5) . . ?
C3 C2 C1 119.9(5) . . ?
C3 C2 C7 117.2(5) . . ?
C7 C2 C1 122.9(5) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.3(6) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(6) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(6) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.7(6) . . ?
C7 C6 H6 119.7 . . ?
O3 C7 C2 121.8(5) . . ?
C6 C7 O3 117.8(5) . . ?
C6 C7 C2 120.4(5) . . ?
O3 C8 C9 115.7(5) . . ?
O3 C8 C13 123.6(5) . . ?
C13 C8 C9 120.6(5) . . ?
C8 C9 C14 120.7(5) . . ?
C10 C9 C8 118.9(5) . . ?
C10 C9 C14 120.2(5) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.3(5) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 118.7(5) . . ?
C10 C11 C15 120.2(5) . . ?
C12 C11 C15 121.1(5) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(5) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 119.6(5) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O4 C14 Dy1 68.6(3) . 2_766 ?
O4 C14 C9 118.4(5) . . ?
O5 C14 Dy1 52.4(3) . 2_766 ?
O5 C14 O4 120.8(5) . . ?
O5 C14 C9 120.6(5) . . ?
C9 C14 Dy1 168.8(4) . 2_766 ?
O6 C15 Dy1 58.5(3) . 2_756 ?
O6 C15 O7 120.5(5) . . ?
O6 C15 C11 119.6(5) . . ?
O7 C15 Dy1 62.1(3) . 2_756 ?
O7 C15 C11 119.9(5) . . ?
C11 C15 Dy1 178.0(4) . 2_756 ?
H16A C16 H16B 109.4 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 105.1 . . ?
C17 C16 H16B 108.6 . . ?
C17 C16 H16C 114.6 . . ?
N1 C17 C16 177.9(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Dy1 O2 C1 O1 -9.1(9) 2_666 . . . ?
Dy1 O2 C1 C2 170.5(4) 2_666 . . . ?
Dy1 O4 C14 Dy1 149.0(7) . . . 2_766 ?
Dy1 O4 C14 O5 153.5(5) . . . . ?
Dy1 O4 C14 O5 4.5(5) 2_766 . . . ?
Dy1 O4 C14 C9 -170.3(4) 2_766 . . . ?
Dy1 O4 C14 C9 -21.3(10) . . . . ?
Dy1 O5 C14 O4 -5.3(6) 2_766 . . . ?
Dy1 O5 C14 C9 169.4(4) 2_766 . . . ?
Dy1 O6 C15 O7 -0.2(6) 2_756 . . . ?
Dy1 O6 C15 C11 179.5(4) 2_756 . . . ?
Dy1 O7 C15 O6 0.2(5) 2_756 . . . ?
Dy1 O7 C15 C11 -179.5(4) 2_756 . . . ?
O1 C1 C2 C3 144.0(6) . . . . ?
O1 C1 C2 C7 -35.7(8) . . . . ?
O2 C1 C2 C3 -35.6(8) . . . . ?
O2 C1 C2 C7 144.6(6) . . . . ?
O3 C8 C9 C10 176.5(5) . . . . ?
O3 C8 C9 C14 -8.6(7) . . . . ?
O3 C8 C13 C12 -176.5(5) . . . . ?
C1 C2 C3 C4 179.6(6) . . . . ?
C1 C2 C7 O3 1.6(8) . . . . ?
C1 C2 C7 C6 -179.7(6) . . . . ?
C2 C3 C4 C5 1.4(11) . . . . ?
C3 C2 C7 O3 -178.2(5) . . . . ?
C3 C2 C7 C6 0.6(9) . . . . ?
C3 C4 C5 C6 -2.0(11) . . . . ?
C4 C5 C6 C7 2.0(11) . . . . ?
C5 C6 C7 O3 177.5(6) . . . . ?
C5 C6 C7 C2 -1.3(10) . . . . ?
C7 O3 C8 C9 178.3(5) . . . . ?
C7 O3 C8 C13 -4.6(8) . . . . ?
C7 C2 C3 C4 -0.7(10) . . . . ?
C8 O3 C7 C2 -76.2(7) . . . . ?
C8 O3 C7 C6 105.0(6) . . . . ?
C8 C9 C10 C11 0.9(8) . . . . ?
C8 C9 C14 Dy1 178.6(16) . . . 2_766 ?
C8 C9 C14 O4 -55.1(7) . . . . ?
C8 C9 C14 O5 130.1(6) . . . . ?
C9 C8 C13 C12 0.5(8) . . . . ?
C9 C10 C11 C12 -0.8(8) . . . . ?
C9 C10 C11 C15 176.5(5) . . . . ?
C10 C9 C14 Dy1 -7(2) . . . 2_766 ?
C10 C9 C14 O4 119.8(6) . . . . ?
C10 C9 C14 O5 -55.0(7) . . . . ?
C10 C11 C12 C13 0.6(9) . . . . ?
C10 C11 C15 O6 -5.0(8) . . . . ?
C10 C11 C15 O7 174.7(5) . . . . ?
C11 C12 C13 C8 -0.4(9) . . . . ?
C12 C11 C15 O6 172.3(5) . . . . ?
C12 C11 C15 O7 -8.1(8) . . . . ?
C13 C8 C9 C10 -0.8(8) . . . . ?
C13 C8 C9 C14 174.2(5) . . . . ?
C14 C9 C10 C11 -174.0(5) . . . . ?
C15 C11 C12 C13 -176.7(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1449728'
_audit_update_record             
;
2016-07-14 deposited with the CCDC.
2016-07-14 downloaded from the CCDC.
;
_audit_creation_date             2016-07-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H11 Gd O9, H2 O, C2 H3 N'
_chemical_formula_sum            'C17 H16 Gd N O10'
_chemical_formula_weight         551.56
_chemical_melting_point          ?
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'
Gd Gd -0.1653 3.9035 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3793(10)
_cell_length_b                   9.7001(11)
_cell_length_c                   12.9527(14)
_cell_angle_alpha                71.987(2)
_cell_angle_beta                 88.658(2)
_cell_angle_gamma                62.2680(10)
_cell_volume                     981.74(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5212
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.221
_cell_measurement_theta_min      2.510
_shelx_estimated_absorpt_T_max   0.664
_shelx_estimated_absorpt_T_min   0.533
_exptl_absorpt_coefficient_mu    3.433
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0350 after correction.
The Ratio of minimum to maximum transmission is 0.6705.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             538
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4784
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.670
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3265
_reflns_number_total             3356
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.034
_refine_diff_density_min         -1.163
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0287
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0432P)²+3.4513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17,
 O1, O2, O3, O4, O5, O6, O7, O8, O9, O10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Riding coordinates:
 O8(H8A,H8B), O9(H9A,H9B), O10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.25875(2) 0.44718(2) 1.01835(2) 0.01267(11) Uani 1 1 d . . . . .
O1 O 0.3740(5) 0.5590(5) 0.8832(3) 0.0243(8) Uani 1 1 d . U . . .
O2 O 0.5606(4) 0.6324(5) 0.8247(3) 0.0239(8) Uani 1 1 d . U . . .
O3 O 0.0908(4) 0.7652(4) 0.7226(3) 0.0195(7) Uani 1 1 d . U . . .
O4 O -0.0143(4) 0.6308(4) 0.9203(3) 0.0176(7) Uani 1 1 d . U . . .
O5 O -0.2717(4) 0.8196(5) 0.8669(3) 0.0259(8) Uani 1 1 d . U . . .
O6 O -0.2268(4) 1.2960(4) 0.9608(3) 0.0209(7) Uani 1 1 d . U . . .
O7 O -0.0956(4) 1.4058(4) 0.8532(3) 0.0212(7) Uani 1 1 d . U . . .
O8 O 0.2161(4) 0.3461(5) 0.8834(4) 0.0331(10) Uani 1 1 d . U . . .
H8A H 0.1225 0.3626 0.8745 0.050 Uiso 1 1 d R . . . .
H8B H 0.2756 0.2704 0.8613 0.050 Uiso 1 1 d R . . . .
O9 O 0.5245(4) 0.2149(5) 1.0105(3) 0.0234(8) Uani 1 1 d . U . . .
H9A H 0.5970 0.2393 0.9953 0.035 Uiso 1 1 d R . . . .
H9B H 0.5400 0.1312 1.0608 0.035 Uiso 1 1 d R . . . .
O10 O 0.4201(6) 0.0867(6) 0.8087(4) 0.0478(12) Uani 1 1 d . U . . .
H10A H 0.5213 0.0352 0.8114 0.072 Uiso 1 1 d R . . . .
H10B H 0.3896 0.1107 0.7437 0.072 Uiso 1 1 d R . . . .
C1 C 0.4409(6) 0.6148(6) 0.8081(4) 0.0159(9) Uani 1 1 d . U . . .
C2 C 0.3719(6) 0.6663(6) 0.6904(4) 0.0174(9) Uani 1 1 d . U . . .
C3 C 0.2083(6) 0.7384(6) 0.6527(4) 0.0189(10) Uani 1 1 d . U . . .
C4 C 0.1539(7) 0.7835(8) 0.5429(5) 0.0301(12) Uani 1 1 d . U . . .
H4 H 0.0432 0.8331 0.5188 0.036 Uiso 1 1 calc R . . . .
C5 C 0.2651(8) 0.7545(8) 0.4687(5) 0.0360(14) Uani 1 1 d . U . . .
H5 H 0.2291 0.7816 0.3953 0.043 Uiso 1 1 calc R . . . .
C6 C 0.4277(8) 0.6858(8) 0.5042(5) 0.0354(14) Uani 1 1 d . U . . .
H6 H 0.5017 0.6703 0.4542 0.042 Uiso 1 1 calc R . . . .
C7 C 0.4824(7) 0.6394(7) 0.6144(4) 0.0265(11) Uani 1 1 d . U . . .
H7 H 0.5932 0.5900 0.6382 0.032 Uiso 1 1 calc R . . . .
C8 C 0.0445(5) 0.8935(6) 0.7614(4) 0.0135(9) Uani 1 1 d . U . . .
C9 C -0.0728(5) 0.9103(6) 0.8329(4) 0.0133(9) Uani 1 1 d . U . . .
C10 C -0.1316(6) 1.0417(6) 0.8714(4) 0.0160(9) Uani 1 1 d . U . . .
H10 H -0.2086 1.0528 0.9192 0.019 Uiso 1 1 calc R . . . .
C11 C -0.0777(6) 1.1573(6) 0.8400(4) 0.0159(9) Uani 1 1 d . U . . .
C12 C 0.0387(6) 1.1393(6) 0.7692(4) 0.0200(10) Uani 1 1 d . U . . .
H12 H 0.0761 1.2161 0.7482 0.024 Uiso 1 1 calc R . . . .
C13 C 0.0992(6) 1.0086(6) 0.7299(4) 0.0184(10) Uani 1 1 d . U . . .
H13 H 0.1766 0.9978 0.6824 0.022 Uiso 1 1 calc R . . . .
C14 C -0.1219(6) 0.7789(6) 0.8749(4) 0.0141(9) Uani 1 1 d . U . . .
C15 C -0.1383(6) 1.2946(6) 0.8868(4) 0.0157(9) Uani 1 1 d . U . . .
C16 C 0.7342(19) 0.814(2) 0.6260(9) 0.117(6) Uani 1 1 d . U . . .
H16A H 0.6330 0.8350 0.6539 0.175 Uiso 1 1 calc GR . . . .
H16B H 0.7602 0.8985 0.6261 0.175 Uiso 1 1 calc GR . . . .
H16C H 0.8190 0.7080 0.6716 0.175 Uiso 1 1 calc GR . . . .
C17 C 0.7193(18) 0.814(2) 0.5125(9) 0.107(5) Uani 1 1 d . U . . .
N1 N 0.6988(16) 0.8242(18) 0.4273(7) 0.118(5) 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 O1 2.289(4) . ?
Gd1 O2 2.361(3) 2_667 ?
Gd1 O4 2.759(3) 2_567 ?
Gd1 O4 2.419(3) . ?
Gd1 O5 2.502(4) 2_567 ?
Gd1 O6 2.467(3) 2_577 ?
Gd1 O7 2.542(3) 2_577 ?
Gd1 O8 2.374(4) . ?
Gd1 O9 2.490(3) . ?
Gd1 C14 3.004(5) 2_567 ?
Gd1 C15 2.875(5) 2_577 ?
O1 C1 1.263(6) . ?
O2 Gd1 2.361(3) 2_667 ?
O2 C1 1.244(6) . ?
O3 C3 1.391(6) . ?
O3 C8 1.365(6) . ?
O4 Gd1 2.759(3) 2_567 ?
O4 C14 1.259(6) . ?
O5 Gd1 2.502(4) 2_567 ?
O5 C14 1.267(6) . ?
O6 Gd1 2.467(3) 2_577 ?
O6 C15 1.253(6) . ?
O7 Gd1 2.542(3) 2_577 ?
O7 C15 1.272(6) . ?
O8 H8A 0.8201 . ?
O8 H8B 0.8198 . ?
O9 H9A 0.8201 . ?
O9 H9B 0.8201 . ?
O10 H10A 0.8372 . ?
O10 H10B 0.8202 . ?
C1 C2 1.506(7) . ?
C2 C3 1.380(7) . ?
C2 C7 1.403(7) . ?
C3 C4 1.384(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.404(6) . ?
C8 C13 1.386(7) . ?
C9 C10 1.380(7) . ?
C9 C14 1.496(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(7) . ?
C11 C12 1.392(7) . ?
C11 C15 1.497(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(7) . ?
C13 H13 0.9300 . ?
C14 Gd1 3.005(5) 2_567 ?
C15 Gd1 2.875(5) 2_577 ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C17 1.481(16) . ?
C17 N1 1.089(13) . ?

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
O1 Gd1 O2 100.85(13) . 2_667 ?
O1 Gd1 O4 149.39(12) . 2_567 ?
O1 Gd1 O4 93.39(12) . . ?
O1 Gd1 O5 143.22(13) . 2_567 ?
O1 Gd1 O6 71.74(13) . 2_577 ?
O1 Gd1 O7 123.18(12) . 2_577 ?
O1 Gd1 O8 81.67(15) . . ?
O1 Gd1 O9 73.34(13) . . ?
O1 Gd1 C14 154.34(13) . 2_567 ?
O1 Gd1 C15 97.27(14) . 2_577 ?
O2 Gd1 O4 109.75(11) 2_667 2_567 ?
O2 Gd1 O4 145.74(12) 2_667 . ?
O2 Gd1 O5 78.05(13) 2_667 2_567 ?
O2 Gd1 O6 73.15(13) 2_667 2_577 ?
O2 Gd1 O7 71.99(13) 2_667 2_577 ?
O2 Gd1 O8 141.60(14) 2_667 . ?
O2 Gd1 O9 72.11(13) 2_667 . ?
O2 Gd1 C14 95.28(13) 2_667 2_567 ?
O2 Gd1 C15 70.12(13) 2_667 2_577 ?
O4 Gd1 O4 60.65(13) . 2_567 ?
O4 Gd1 O5 108.09(12) . 2_567 ?
O4 Gd1 O6 82.23(12) . 2_577 ?
O4 Gd1 O7 74.12(12) . 2_577 ?
O4 Gd1 O9 142.13(12) . . ?
O4 Gd1 C14 84.05(12) . 2_567 ?
O4 Gd1 C14 24.76(12) 2_567 2_567 ?
O4 Gd1 C15 92.62(12) 2_567 2_577 ?
O4 Gd1 C15 77.32(12) . 2_577 ?
O5 Gd1 O4 49.13(11) 2_567 2_567 ?
O5 Gd1 O7 91.86(12) 2_567 2_577 ?
O5 Gd1 C14 24.48(13) 2_567 2_567 ?
O5 Gd1 C15 116.06(13) 2_567 2_577 ?
O6 Gd1 O4 116.21(11) 2_577 2_567 ?
O6 Gd1 O5 139.06(13) 2_577 2_567 ?
O6 Gd1 O7 51.92(11) 2_577 2_577 ?
O6 Gd1 O9 123.96(12) 2_577 . ?
O6 Gd1 C14 132.65(12) 2_577 2_567 ?
O6 Gd1 C15 25.70(13) 2_577 2_577 ?
O7 Gd1 O4 68.15(10) 2_577 2_567 ?
O7 Gd1 C14 80.74(12) 2_577 2_567 ?
O7 Gd1 C15 26.23(13) 2_577 2_577 ?
O8 Gd1 O4 74.86(12) . 2_567 ?
O8 Gd1 O4 70.97(12) . . ?
O8 Gd1 O5 77.87(15) . 2_567 ?
O8 Gd1 O6 140.84(14) . 2_577 ?
O8 Gd1 O7 138.09(12) . 2_577 ?
O8 Gd1 O9 72.07(13) . . ?
O8 Gd1 C14 73.35(14) . 2_567 ?
O8 Gd1 C15 148.12(13) . 2_577 ?
O9 Gd1 O4 116.28(11) . 2_567 ?
O9 Gd1 O5 71.42(12) . 2_567 ?
O9 Gd1 O7 142.79(13) . 2_577 ?
O9 Gd1 C14 93.13(12) . 2_567 ?
O9 Gd1 C15 138.41(13) . 2_577 ?
C15 Gd1 C14 106.97(13) 2_577 2_567 ?
C1 O1 Gd1 177.6(3) . . ?
C1 O2 Gd1 134.4(3) . 2_667 ?
C8 O3 C3 119.5(4) . . ?
Gd1 O4 Gd1 119.35(13) . 2_567 ?
C14 O4 Gd1 88.6(3) . 2_567 ?
C14 O4 Gd1 145.8(3) . . ?
C14 O5 Gd1 100.6(3) . 2_567 ?
C15 O6 Gd1 95.7(3) . 2_577 ?
C15 O7 Gd1 91.7(3) . 2_577 ?
Gd1 O8 H8A 112.7 . . ?
Gd1 O8 H8B 133.5 . . ?
H8A O8 H8B 108.8 . . ?
Gd1 O9 H9A 114.9 . . ?
Gd1 O9 H9B 108.3 . . ?
H9A O9 H9B 121.9 . . ?
H10A O10 H10B 101.3 . . ?
O1 C1 C2 118.8(4) . . ?
O2 C1 O1 124.3(5) . . ?
O2 C1 C2 117.0(4) . . ?
C3 C2 C1 124.4(4) . . ?
C3 C2 C7 118.3(5) . . ?
C7 C2 C1 117.3(4) . . ?
C2 C3 O3 122.2(4) . . ?
C2 C3 C4 121.1(5) . . ?
C4 C3 O3 116.6(5) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(5) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(5) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(5) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 H7 119.7 . . ?
C6 C7 C2 120.6(5) . . ?
C6 C7 H7 119.7 . . ?
O3 C8 C9 115.9(4) . . ?
O3 C8 C13 124.0(4) . . ?
C13 C8 C9 120.0(4) . . ?
C8 C9 C14 120.3(4) . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 C14 120.3(4) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 119.2(4) . . ?
C10 C11 C15 119.9(4) . . ?
C12 C11 C15 120.8(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(5) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.9(4) . . ?
C12 C13 H13 120.1 . . ?
O4 C14 Gd1 66.7(2) . 2_567 ?
O4 C14 O5 121.2(4) . . ?
O4 C14 C9 119.5(4) . . ?
O5 C14 Gd1 54.9(2) . 2_567 ?
O5 C14 C9 119.2(4) . . ?
C9 C14 Gd1 169.8(3) . 2_567 ?
O6 C15 Gd1 58.6(2) . 2_577 ?
O6 C15 O7 120.7(4) . . ?
O6 C15 C11 119.6(4) . . ?
O7 C15 Gd1 62.1(2) . 2_577 ?
O7 C15 C11 119.7(4) . . ?
C11 C15 Gd1 178.2(3) . 2_577 ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
N1 C17 C16 175(2) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
