# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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 1422769'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H17 Eu N2 O8'
_chemical_formula_weight         649.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'Pbca  '

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

_cell_length_a                   10.2928(13)
_cell_length_b                   20.805(3)
_cell_length_c                   21.558(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4616.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4184
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      25.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2559
_exptl_absorpt_coefficient_mu    2.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14452
_diffrn_reflns_av_R_equivalents  0.1946
_diffrn_reflns_av_sigmaI/netI    0.1867
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.37
_diffrn_reflns_theta_max         25.36
_reflns_number_total             4184
_reflns_number_gt                1966
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4184
_refine_ls_number_parameters     346
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.2005
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.102
_refine_ls_shift/su_mean         0.003

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 0.09114(8) 0.02877(4) 0.07584(4) 0.0217(3) Uani 1 1 d . . .
N1 N 0.2430(14) 0.1135(7) 0.1242(8) 0.030(4) Uani 1 1 d . . .
N2 N 0.0649(14) 0.0492(7) 0.1922(7) 0.026(4) Uani 1 1 d . . .
O1 O 0.5892(11) 0.1659(6) -0.1431(5) 0.027(3) Uani 1 1 d . . .
O2 O 0.8503(13) 0.0738(6) -0.1310(6) 0.037(3) Uani 1 1 d . . .
O3 O 0.6971(10) 0.0272(6) -0.0774(6) 0.028(3) Uani 1 1 d . . .
O4 O 0.9220(12) 0.0584(5) -0.0043(5) 0.027(3) Uani 1 1 d . . .
O5 O 0.9555(10) 0.1285(5) 0.0717(6) 0.018(2) Uani 1 1 d . . .
O6 O 0.1036(11) 0.0246(6) -0.0968(5) 0.025(3) Uani 1 1 d . . .
O7 O 0.1956(11) 0.0727(6) -0.0140(5) 0.028(3) Uani 1 1 d . . .
OW1 O 0.472(4) -0.0435(13) -0.0239(16) 0.200(16) Uani 1 1 d . . .
HW1A H 0.4541 -0.0755 -0.0469 0.300 Uiso 1 1 d R . .
HW1B H 0.5026 -0.0133 -0.0461 0.300 Uiso 1 1 d R . .
C1 C 0.6385(16) 0.1796(9) -0.0850(9) 0.025(4) Uani 1 1 d . . .
C2 C 0.7316(15) 0.1374(8) -0.0587(8) 0.023(4) Uani 1 1 d . . .
C3 C 0.7934(16) 0.1534(9) -0.0039(8) 0.025(4) Uani 1 1 d . . .
C4 C 0.7635(17) 0.2120(9) 0.0261(9) 0.028(4) Uani 1 1 d . . .
H4A H 0.8079 0.2248 0.0628 0.034 Uiso 1 1 calc R . .
C5 C 0.6642(18) 0.2516(10) -0.0004(9) 0.027(4) Uani 1 1 d . . .
H5A H 0.6386 0.2895 0.0208 0.032 Uiso 1 1 calc R . .
C6 C 0.6043(16) 0.2364(8) -0.0559(9) 0.031(5) Uani 1 1 d . . .
H6A H 0.5412 0.2643 -0.0735 0.037 Uiso 1 1 calc R . .
C7 C 0.7608(19) 0.0761(9) -0.0915(8) 0.030(5) Uani 1 1 d . . .
C8 C 0.8964(19) 0.1119(8) 0.0222(8) 0.028(4) Uani 1 1 d . . .
C9 C 0.4597(17) 0.1509(8) -0.1499(8) 0.023(4) Uani 1 1 d . . .
C10 C 0.3880(18) 0.1213(9) -0.1025(9) 0.027(4) Uani 1 1 d . . .
H10B H 0.428(18) 0.114(8) -0.057(9) 0.033 Uiso 1 1 d . . .
C11 C 0.2566(16) 0.1051(8) -0.1174(8) 0.022(4) Uani 1 1 d . . .
C12 C 0.2033(19) 0.1218(9) -0.1728(9) 0.033(5) Uani 1 1 d . . .
H12A H 0.1141 0.1129 -0.1802 0.039 Uiso 1 1 calc R . .
C13 C 0.2780(19) 0.1525(9) -0.2200(10) 0.041(5) Uani 1 1 d . . .
H13A H 0.2409 0.1635 -0.2589 0.049 Uiso 1 1 calc R . .
C14 C 0.406(2) 0.1654(8) -0.2067(9) 0.034(4) Uani 1 1 d . . .
H14A H 0.4595 0.1848 -0.2376 0.041 Uiso 1 1 calc R . .
C15 C 0.1798(15) 0.0648(8) -0.0691(8) 0.020(4) Uani 1 1 d U . .
C16 C 0.3315(18) 0.1458(10) 0.0902(10) 0.037(5) Uani 1 1 d . . .
H16A H 0.3352 0.1388 0.0467 0.044 Uiso 1 1 calc R . .
C17 C 0.417(2) 0.1891(10) 0.1172(10) 0.046(5) Uani 1 1 d U . .
H17A H 0.4745 0.2138 0.0920 0.055 Uiso 1 1 calc R . .
C18 C 0.419(2) 0.1961(9) 0.1803(10) 0.039(5) Uani 1 1 d . . .
H18A H 0.4808 0.2242 0.1989 0.047 Uiso 1 1 calc R . .
C19 C 0.3320(18) 0.1625(9) 0.2179(10) 0.031(5) Uani 1 1 d . . .
C20 C 0.332(2) 0.1644(11) 0.2840(11) 0.047(6) Uani 1 1 d . . .
H20A H 0.3914 0.1924 0.3041 0.057 Uiso 1 1 calc R . .
C21 C 0.2534(19) 0.1297(10) 0.3186(9) 0.037(5) Uani 1 1 d . . .
H21A H 0.2584 0.1319 0.3626 0.045 Uiso 1 1 calc R . .
C22 C 0.1575(18) 0.0873(9) 0.2883(9) 0.031(5) Uani 1 1 d . . .
C23 C 0.0704(18) 0.0493(9) 0.3225(10) 0.034(5) Uani 1 1 d U . .
H23A H 0.0735 0.0486 0.3665 0.041 Uiso 1 1 calc R . .
C24 C -0.018(2) 0.0138(10) 0.2913(10) 0.044(6) Uani 1 1 d . . .
H24A H -0.0788 -0.0114 0.3137 0.053 Uiso 1 1 calc R . .
C25 C -0.0208(16) 0.0138(8) 0.2271(9) 0.029(4) Uani 1 1 d . . .
H25A H -0.0841 -0.0116 0.2064 0.035 Uiso 1 1 calc R . .
C26 C 0.1527(19) 0.0863(10) 0.2246(9) 0.032(5) Uani 1 1 d . . .
C27 C 0.2469(17) 0.1204(10) 0.1855(9) 0.031(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 O6 2.335(11) 5 ?
Eu1 O4 2.383(12) 5_655 ?
Eu1 O7 2.396(12) . ?
Eu1 O3 2.472(10) 5_655 ?
Eu1 O5 2.503(10) 1_455 ?
Eu1 O2 2.516(13) 5_655 ?
Eu1 O4 2.529(12) 1_455 ?
Eu1 N2 2.559(14) . ?
Eu1 N1 2.576(15) . ?
Eu1 C7 2.683(19) 5_655 ?
Eu1 C8 2.889(19) 1_455 ?
Eu1 Eu1 3.9556(17) 5 ?
N1 C27 1.33(2) . ?
N1 C16 1.35(2) . ?
N2 C25 1.37(2) . ?
N2 C26 1.38(2) . ?
O1 C9 1.38(2) . ?
O1 C1 1.38(2) . ?
O2 C7 1.25(2) . ?
O2 Eu1 2.516(13) 5_655 ?
O3 C7 1.25(2) . ?
O3 Eu1 2.472(10) 5_655 ?
O4 C8 1.28(2) . ?
O4 Eu1 2.383(12) 5_655 ?
O4 Eu1 2.530(12) 1_655 ?
O5 C8 1.28(2) . ?
O5 Eu1 2.503(10) 1_655 ?
O6 C15 1.294(19) . ?
O6 Eu1 2.335(11) 5 ?
O7 C15 1.21(2) . ?
OW1 HW1A 0.8496 . ?
OW1 HW1B 0.8500 . ?
C1 C6 1.38(2) . ?
C1 C2 1.42(2) . ?
C2 C3 1.38(2) . ?
C2 C7 1.49(2) . ?
C3 C4 1.42(2) . ?
C3 C8 1.48(3) . ?
C4 C5 1.43(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.38(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 Eu1 2.683(19) 5_655 ?
C8 Eu1 2.889(19) 1_655 ?
C9 C14 1.38(2) . ?
C9 C10 1.40(2) . ?
C10 C11 1.43(2) . ?
C10 H10B 1.08(19) . ?
C11 C12 1.36(2) . ?
C11 C15 1.55(2) . ?
C12 C13 1.43(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.38(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C16 C17 1.39(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.37(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.40(3) . ?
C18 H18A 0.9500 . ?
C19 C27 1.42(3) . ?
C19 C20 1.43(3) . ?
C20 C21 1.32(3) . ?
C20 H20A 0.9500 . ?
C21 C22 1.48(3) . ?
C21 H21A 0.9500 . ?
C22 C26 1.37(3) . ?
C22 C23 1.40(3) . ?
C23 C24 1.35(3) . ?
C23 H23A 0.9500 . ?
C24 C25 1.38(3) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C27 1.47(3) . ?

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
O6 Eu1 O4 73.4(4) 5 5_655 ?
O6 Eu1 O7 136.3(4) 5 . ?
O4 Eu1 O7 78.0(4) 5_655 . ?
O6 Eu1 O3 122.0(4) 5 5_655 ?
O4 Eu1 O3 72.5(4) 5_655 5_655 ?
O7 Eu1 O3 78.2(4) . 5_655 ?
O6 Eu1 O5 85.5(4) 5 1_455 ?
O4 Eu1 O5 125.2(4) 5_655 1_455 ?
O7 Eu1 O5 84.6(4) . 1_455 ?
O3 Eu1 O5 152.0(4) 5_655 1_455 ?
O6 Eu1 O2 73.2(4) 5 5_655 ?
O4 Eu1 O2 71.0(4) 5_655 5_655 ?
O7 Eu1 O2 126.7(4) . 5_655 ?
O3 Eu1 O2 51.9(4) 5_655 5_655 ?
O5 Eu1 O2 148.6(4) 1_455 5_655 ?
O6 Eu1 O4 69.9(4) 5 1_455 ?
O4 Eu1 O4 72.8(4) 5_655 1_455 ?
O7 Eu1 O4 70.3(4) . 1_455 ?
O3 Eu1 O4 136.9(4) 5_655 1_455 ?
O5 Eu1 O4 52.4(4) 1_455 1_455 ?
O2 Eu1 O4 134.0(4) 5_655 1_455 ?
O6 Eu1 N2 78.4(4) 5 . ?
O4 Eu1 N2 139.0(4) 5_655 . ?
O7 Eu1 N2 140.9(4) . . ?
O3 Eu1 N2 99.1(4) 5_655 . ?
O5 Eu1 N2 80.7(4) 1_455 . ?
O2 Eu1 N2 72.7(5) 5_655 . ?
O4 Eu1 N2 123.8(4) 1_455 . ?
O6 Eu1 N1 140.2(5) 5 . ?
O4 Eu1 N1 144.7(5) 5_655 . ?
O7 Eu1 N1 78.1(5) . . ?
O3 Eu1 N1 77.4(4) 5_655 . ?
O5 Eu1 N1 77.6(4) 1_455 . ?
O2 Eu1 N1 104.1(5) 5_655 . ?
O4 Eu1 N1 121.8(4) 1_455 . ?
N2 Eu1 N1 63.5(5) . . ?
O6 Eu1 C7 94.4(5) 5 5_655 ?
O4 Eu1 C7 59.7(5) 5_655 5_655 ?
O7 Eu1 C7 99.0(5) . 5_655 ?
O3 Eu1 C7 27.6(5) 5_655 5_655 ?
O5 Eu1 C7 174.7(4) 1_455 5_655 ?
O2 Eu1 C7 27.7(5) 5_655 5_655 ?
O4 Eu1 C7 132.5(5) 1_455 5_655 ?
N2 Eu1 C7 94.1(5) . 5_655 ?
N1 Eu1 C7 99.2(5) . 5_655 ?
O6 Eu1 C8 76.5(5) 5 1_455 ?
O4 Eu1 C8 99.0(5) 5_655 1_455 ?
O7 Eu1 C8 76.1(5) . 1_455 ?
O3 Eu1 C8 154.1(5) 5_655 1_455 ?
O5 Eu1 C8 26.2(4) 1_455 1_455 ?
O2 Eu1 C8 149.7(5) 5_655 1_455 ?
O4 Eu1 C8 26.3(4) 1_455 1_455 ?
N2 Eu1 C8 102.7(5) . 1_455 ?
N1 Eu1 C8 100.0(5) . 1_455 ?
C7 Eu1 C8 158.7(5) 5_655 1_455 ?
O6 Eu1 Eu1 67.0(3) 5 5 ?
O4 Eu1 Eu1 37.6(3) 5_655 5 ?
O7 Eu1 Eu1 70.1(3) . 5 ?
O3 Eu1 Eu1 106.6(3) 5_655 5 ?
O5 Eu1 Eu1 87.5(3) 1_455 5 ?
O2 Eu1 Eu1 104.3(3) 5_655 5 ?
O4 Eu1 Eu1 35.1(3) 1_455 5 ?
N2 Eu1 Eu1 144.2(3) . 5 ?
N1 Eu1 Eu1 146.0(4) . 5 ?
C7 Eu1 Eu1 97.3(4) 5_655 5 ?
C8 Eu1 Eu1 61.4(3) 1_455 5 ?
C27 N1 C16 117.8(16) . . ?
C27 N1 Eu1 119.6(13) . . ?
C16 N1 Eu1 122.1(13) . . ?
C25 N2 C26 116.4(15) . . ?
C25 N2 Eu1 121.0(11) . . ?
C26 N2 Eu1 121.4(12) . . ?
C9 O1 C1 119.9(13) . . ?
C7 O2 Eu1 83.6(11) . 5_655 ?
C7 O3 Eu1 85.6(10) . 5_655 ?
C8 O4 Eu1 160.0(12) . 5_655 ?
C8 O4 Eu1 92.7(11) . 1_655 ?
Eu1 O4 Eu1 107.2(4) 5_655 1_655 ?
C8 O5 Eu1 94.1(10) . 1_655 ?
C15 O6 Eu1 137.6(10) . 5 ?
C15 O7 Eu1 133.0(11) . . ?
HW1A OW1 HW1B 109.5 . . ?
O1 C1 C6 119.6(16) . . ?
O1 C1 C2 118.8(16) . . ?
C6 C1 C2 121.4(17) . . ?
C3 C2 C1 120.2(16) . . ?
C3 C2 C7 121.2(16) . . ?
C1 C2 C7 118.6(16) . . ?
C2 C3 C4 119.8(17) . . ?
C2 C3 C8 121.0(16) . . ?
C4 C3 C8 119.0(15) . . ?
C3 C4 C5 117.9(17) . . ?
C3 C4 H4A 121.0 . . ?
C5 C4 H4A 121.0 . . ?
C6 C5 C4 122.3(19) . . ?
C6 C5 H5A 118.9 . . ?
C4 C5 H5A 118.9 . . ?
C5 C6 C1 118.2(18) . . ?
C5 C6 H6A 120.9 . . ?
C1 C6 H6A 120.9 . . ?
O3 C7 O2 121.4(17) . . ?
O3 C7 C2 118.4(16) . . ?
O2 C7 C2 120.1(16) . . ?
O3 C7 Eu1 66.7(9) . 5_655 ?
O2 C7 Eu1 68.8(10) . 5_655 ?
C2 C7 Eu1 138.7(12) . 5_655 ?
O5 C8 O4 120.8(17) . . ?
O5 C8 C3 120.2(15) . . ?
O4 C8 C3 119.0(16) . . ?
O5 C8 Eu1 59.8(9) . 1_655 ?
O4 C8 Eu1 61.0(9) . 1_655 ?
C3 C8 Eu1 178.0(13) . 1_655 ?
O1 C9 C14 115.5(16) . . ?
O1 C9 C10 122.1(16) . . ?
C14 C9 C10 122.4(17) . . ?
C9 C10 C11 116.0(17) . . ?
C9 C10 H10B 122(10) . . ?
C11 C10 H10B 122(10) . . ?
C12 C11 C10 121.2(17) . . ?
C12 C11 C15 121.5(16) . . ?
C10 C11 C15 117.3(15) . . ?
C11 C12 C13 121.6(18) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
C14 C13 C12 117.1(19) . . ?
C14 C13 H13A 121.4 . . ?
C12 C13 H13A 121.4 . . ?
C9 C14 C13 121.6(19) . . ?
C9 C14 H14A 119.2 . . ?
C13 C14 H14A 119.2 . . ?
O7 C15 O6 128.5(16) . . ?
O7 C15 C11 121.1(15) . . ?
O6 C15 C11 110.3(15) . . ?
N1 C16 C17 122(2) . . ?
N1 C16 H16A 119.2 . . ?
C17 C16 H16A 119.2 . . ?
C18 C17 C16 120(2) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 121(2) . . ?
C17 C18 H18A 119.5 . . ?
C19 C18 H18A 119.5 . . ?
C18 C19 C27 114.8(18) . . ?
C18 C19 C20 124.5(19) . . ?
C27 C19 C20 120.5(19) . . ?
C21 C20 C19 124(2) . . ?
C21 C20 H20A 118.2 . . ?
C19 C20 H20A 118.2 . . ?
C20 C21 C22 119.1(19) . . ?
C20 C21 H21A 120.4 . . ?
C22 C21 H21A 120.4 . . ?
C26 C22 C23 119.5(19) . . ?
C26 C22 C21 118.5(19) . . ?
C23 C22 C21 122.0(18) . . ?
C24 C23 C22 118(2) . . ?
C24 C23 H23A 120.8 . . ?
C22 C23 H23A 120.8 . . ?
C23 C24 C25 121(2) . . ?
C23 C24 H24A 119.6 . . ?
C25 C24 H24A 119.6 . . ?
N2 C25 C24 122.2(18) . . ?
N2 C25 H25A 118.9 . . ?
C24 C25 H25A 118.9 . . ?
C22 C26 N2 122.7(18) . . ?
C22 C26 C27 122.8(17) . . ?
N2 C26 C27 114.3(16) . . ?
N1 C27 C19 125.0(18) . . ?
N1 C27 C26 119.9(17) . . ?
C19 C27 C26 115.0(17) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         3.253
_refine_diff_density_min         -2.624
_refine_diff_density_rms         0.272
####################################################################### 
# 
# 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 1422770'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H12 Eu O11'
_chemical_formula_sum            'C16 H12 Eu O11'
_chemical_formula_weight         532.22

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic'
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   5.9993(4)
_cell_length_b                   9.8736(7)
_cell_length_c                   14.8861(10)
_cell_angle_alpha                85.728(2)
_cell_angle_beta                 89.493(2)
_cell_angle_gamma                74.842(3)
_cell_volume                     848.68(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4491
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      25.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.083
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             518
_exptl_absorpt_coefficient_mu    3.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5058
_exptl_absorpt_correction_T_max  0.7050
_exptl_absorpt_process_details   'TWINABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal monochromator'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3015
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         25.43
_reflns_number_total             3015
_reflns_number_gt                2648
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0175P)²+3.9626P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3015
_refine_ls_number_parameters     266
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0669
_refine_ls_wR_factor_gt          0.0623
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1704(10) 0.4522(6) 0.2097(4) 0.0143(13) Uani 1 1 d . . .
C2 C 0.2983(9) 0.4890(6) 0.2768(3) 0.0123(12) Uani 1 1 d . . .
C3 C 0.4517(10) 0.5698(6) 0.2525(3) 0.0118(12) Uani 1 1 d . . .
C4 C 0.4710(11) 0.6133(7) 0.1623(4) 0.0181(14) Uani 1 1 d . . .
H4 H 0.5749 0.6686 0.1456 0.022 Uiso 1 1 calc R . .
C5 C 0.3395(11) 0.5766(7) 0.0967(4) 0.0211(15) Uani 1 1 d . . .
H5 H 0.3524 0.6074 0.0354 0.025 Uiso 1 1 calc R . .
C6 C 0.1893(11) 0.4950(7) 0.1208(4) 0.0217(15) Uani 1 1 d . . .
H6 H 0.1001 0.4689 0.0760 0.026 Uiso 1 1 calc R . .
C7 C 0.2699(9) 0.4316(6) 0.3717(3) 0.0105(11) Uani 1 1 d . . .
C8 C 0.5934(9) 0.6128(6) 0.3219(3) 0.0102(11) Uani 1 1 d . . .
C9 C 0.0477(10) 0.2431(7) 0.2069(4) 0.0170(13) Uani 1 1 d . . .
C10 C -0.1269(11) 0.2138(7) 0.1569(4) 0.0175(14) Uani 1 1 d . . .
H10 H -0.2643 0.2849 0.1413 0.021 Uiso 1 1 calc R . .
C11 C -0.0955(11) 0.0775(7) 0.1303(4) 0.0184(14) Uani 1 1 d . . .
C12 C 0.1060(12) -0.0263(7) 0.1541(4) 0.0224(15) Uani 1 1 d . . .
H12 H 0.1268 -0.1188 0.1355 0.027 Uiso 1 1 calc R . .
C13 C 0.2773(11) 0.0053(7) 0.2051(4) 0.0229(15) Uani 1 1 d . . .
H13 H 0.4135 -0.0657 0.2223 0.027 Uiso 1 1 calc R . .
C14 C 0.2471(11) 0.1413(7) 0.2306(4) 0.0210(14) Uani 1 1 d . . .
H14 H 0.3641 0.1641 0.2644 0.025 Uiso 1 1 calc R . .
C15 C -0.2751(12) 0.0468(8) 0.0728(4) 0.0203(15) Uani 1 1 d . . .
C16 C 0.4017(9) 0.9867(5) 0.4725(3) 0.0091(11) Uani 1 1 d . . .
Eu1 Eu 0.82474(5) 0.70723(3) 0.458567(19) 0.01034(9) Uani 1 1 d . . .
O1 O 0.0080(7) 0.3790(4) 0.2359(3) 0.0182(9) Uani 1 1 d . . .
O2 O 0.1173(6) 0.5025(4) 0.4220(2) 0.0123(8) Uani 1 1 d . . .
O3 O 0.3842(6) 0.3110(4) 0.3978(2) 0.0139(8) Uani 1 1 d . . .
O4 O 0.7147(7) 0.6956(4) 0.3002(2) 0.0158(9) Uani 1 1 d . . .
O5 O 0.5846(6) 0.5650(4) 0.4037(2) 0.0125(8) Uani 1 1 d . . .
O6 O -0.4373(8) 0.1446(5) 0.0398(3) 0.0266(11) Uani 1 1 d . . .
O7 O -0.2487(8) -0.0838(5) 0.0600(3) 0.0291(12) Uani 1 1 d . . .
H7A H -0.3556 -0.1092 0.0244 0.035 Uiso 1 1 d R . .
O8 O 0.4494(6) 0.8751(4) 0.4309(2) 0.0156(8) Uani 1 1 d . . .
O9 O 0.2106(7) 1.0734(4) 0.4731(3) 0.0191(9) Uani 1 1 d . . .
O10 O 1.1498(7) 0.7042(4) 0.5512(3) 0.0208(9) Uani 1 1 d D . .
H10A H 1.241(9) 0.633(4) 0.571(4) 0.025 Uiso 1 1 d D . .
H10B H 1.167(11) 0.776(4) 0.568(4) 0.025 Uiso 1 1 d D . .
O11 O 1.0472(8) 0.8283(5) 0.3626(3) 0.0235(10) Uani 1 1 d D . .
H11A H 1.166(7) 0.845(7) 0.380(4) 0.028 Uiso 1 1 d D . .
H11B H 1.026(11) 0.845(7) 0.3086(16) 0.028 Uiso 1 1 d 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
C1 C6 1.373(8) . ?
C1 C2 1.389(7) . ?
C1 O1 1.394(7) . ?
C2 C3 1.396(8) . ?
C2 C7 1.508(7) . ?
C3 C4 1.392(8) . ?
C3 C8 1.496(7) . ?
C4 C5 1.387(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O3 1.244(7) . ?
C7 O2 1.273(6) . ?
C7 Eu1 2.907(5) 2_666 ?
C8 O4 1.253(6) . ?
C8 O5 1.279(6) . ?
C8 Eu1 2.818(5) . ?
C9 C14 1.375(9) . ?
C9 C10 1.392(8) . ?
C9 O1 1.401(7) . ?
C10 C11 1.396(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(9) . ?
C11 C15 1.487(8) . ?
C12 C13 1.396(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(9) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O6 1.252(8) . ?
C15 O7 1.286(8) . ?
C16 O9 1.239(6) . ?
C16 O8 1.270(6) . ?
C16 C16 1.530(10) 2_676 ?
C16 Eu1 3.213(5) 2_676 ?
C16 Eu1 3.242(5) . ?
Eu1 O10 2.391(4) . ?
Eu1 O2 2.398(4) 1_655 ?
Eu1 O11 2.408(4) . ?
Eu1 O9 2.420(4) 2_676 ?
Eu1 O8 2.439(4) . ?
Eu1 O5 2.442(4) . ?
Eu1 O4 2.473(4) . ?
Eu1 O3 2.487(3) 2_666 ?
Eu1 O2 2.580(4) 2_666 ?
Eu1 C7 2.907(5) 2_666 ?
Eu1 C16 3.213(5) 2_676 ?
O2 Eu1 2.398(4) 1_455 ?
O2 Eu1 2.580(4) 2_666 ?
O3 Eu1 2.487(3) 2_666 ?
O7 H7A 0.9300 . ?
O9 Eu1 2.420(4) 2_676 ?
O10 H10A 0.81(2) . ?
O10 H10B 0.81(2) . ?
O11 H11A 0.82(2) . ?
O11 H11B 0.81(2) . ?

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
C6 C1 C2 121.6(5) . . ?
C6 C1 O1 120.3(5) . . ?
C2 C1 O1 118.0(5) . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 C7 116.9(5) . . ?
C3 C2 C7 124.1(5) . . ?
C4 C3 C2 119.6(5) . . ?
C4 C3 C8 119.2(5) . . ?
C2 C3 C8 121.3(5) . . ?
C5 C4 C3 120.4(5) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 119.6(5) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O3 C7 O2 120.6(5) . . ?
O3 C7 C2 119.5(5) . . ?
O2 C7 C2 119.7(5) . . ?
O3 C7 Eu1 58.2(3) . 2_666 ?
O2 C7 Eu1 62.5(3) . 2_666 ?
C2 C7 Eu1 170.8(3) . 2_666 ?
O4 C8 O5 121.0(5) . . ?
O4 C8 C3 120.5(5) . . ?
O5 C8 C3 118.4(4) . . ?
O4 C8 Eu1 61.3(3) . . ?
O5 C8 Eu1 59.9(3) . . ?
C3 C8 Eu1 175.1(4) . . ?
C14 C9 C10 121.6(6) . . ?
C14 C9 O1 121.0(5) . . ?
C10 C9 O1 117.3(5) . . ?
C9 C10 C11 118.5(6) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 120.3(6) . . ?
C12 C11 C15 120.7(6) . . ?
C10 C11 C15 119.0(6) . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.5(6) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C9 C14 C13 120.0(6) . . ?
C9 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
O6 C15 O7 124.1(6) . . ?
O6 C15 C11 120.4(6) . . ?
O7 C15 C11 115.4(6) . . ?
O9 C16 O8 125.6(5) . . ?
O9 C16 C16 118.1(5) . 2_676 ?
O8 C16 C16 116.3(6) . 2_676 ?
O9 C16 Eu1 41.1(2) . 2_676 ?
O8 C16 Eu1 165.5(4) . 2_676 ?
C16 C16 Eu1 77.4(4) 2_676 2_676 ?
O9 C16 Eu1 165.6(4) . . ?
O8 C16 Eu1 41.4(2) . . ?
C16 C16 Eu1 75.2(4) 2_676 . ?
Eu1 C16 Eu1 152.58(17) 2_676 . ?
O10 Eu1 O2 74.88(13) . 1_655 ?
O10 Eu1 O11 76.81(14) . . ?
O2 Eu1 O11 83.19(14) 1_655 . ?
O10 Eu1 O9 66.95(14) . 2_676 ?
O2 Eu1 O9 139.61(13) 1_655 2_676 ?
O11 Eu1 O9 75.92(14) . 2_676 ?
O10 Eu1 O8 133.43(13) . . ?
O2 Eu1 O8 151.24(12) 1_655 . ?
O11 Eu1 O8 97.34(15) . . ?
O9 Eu1 O8 66.83(13) 2_676 . ?
O10 Eu1 O5 144.81(13) . . ?
O2 Eu1 O5 79.72(12) 1_655 . ?
O11 Eu1 O5 124.01(13) . . ?
O9 Eu1 O5 140.43(13) 2_676 . ?
O8 Eu1 O5 76.24(12) . . ?
O10 Eu1 O4 141.75(14) . . ?
O2 Eu1 O4 80.52(13) 1_655 . ?
O11 Eu1 O4 71.52(13) . . ?
O9 Eu1 O4 123.06(13) 2_676 . ?
O8 Eu1 O4 72.54(13) . . ?
O5 Eu1 O4 53.27(12) . . ?
O10 Eu1 O3 85.91(14) . 2_666 ?
O2 Eu1 O3 116.85(12) 1_655 2_666 ?
O11 Eu1 O3 149.24(13) . 2_666 ?
O9 Eu1 O3 73.93(13) 2_676 2_666 ?
O8 Eu1 O3 76.27(12) . 2_666 ?
O5 Eu1 O3 84.24(12) . 2_666 ?
O4 Eu1 O3 131.75(12) . 2_666 ?
O10 Eu1 O2 71.57(13) . 2_666 ?
O2 Eu1 O2 65.79(13) 1_655 2_666 ?
O11 Eu1 O2 140.17(14) . 2_666 ?
O9 Eu1 O2 111.72(12) 2_676 2_666 ?
O8 Eu1 O2 121.96(12) . 2_666 ?
O5 Eu1 O2 76.00(11) . 2_666 ?
O4 Eu1 O2 123.32(12) . 2_666 ?
O3 Eu1 O2 51.07(12) 2_666 2_666 ?
O10 Eu1 C8 154.68(15) . . ?
O2 Eu1 C8 79.95(14) 1_655 . ?
O11 Eu1 C8 97.68(14) . . ?
O9 Eu1 C8 136.37(15) 2_676 . ?
O8 Eu1 C8 71.45(14) . . ?
O5 Eu1 C8 26.94(13) . . ?
O4 Eu1 C8 26.37(13) . . ?
O3 Eu1 C8 108.25(13) 2_666 . ?
O2 Eu1 C8 100.61(13) 2_666 . ?
O10 Eu1 C7 76.59(14) . 2_666 ?
O2 Eu1 C7 91.74(14) 1_655 2_666 ?
O11 Eu1 C7 153.33(14) . 2_666 ?
O9 Eu1 C7 91.89(14) 2_676 2_666 ?
O8 Eu1 C7 99.47(14) . 2_666 ?
O5 Eu1 C7 80.30(13) . 2_666 ?
O4 Eu1 C7 133.56(13) . 2_666 ?
O3 Eu1 C7 25.17(13) 2_666 2_666 ?
O2 Eu1 C7 25.96(13) 2_666 2_666 ?
C8 Eu1 C7 107.22(14) . 2_666 ?
O10 Eu1 C16 86.01(14) . 2_676 ?
O2 Eu1 C16 159.12(13) 1_655 2_676 ?
O11 Eu1 C16 84.33(14) . 2_676 ?
O9 Eu1 C16 19.66(13) 2_676 2_676 ?
O8 Eu1 C16 47.48(12) . 2_676 ?
O5 Eu1 C16 121.17(12) . 2_676 ?
O4 Eu1 C16 111.14(13) . 2_676 ?
O3 Eu1 C16 69.07(12) 2_666 2_676 ?
O2 Eu1 C16 116.32(12) 2_666 2_676 ?
C8 Eu1 C16 118.37(14) . 2_676 ?
C7 Eu1 C16 91.93(14) 2_666 2_676 ?
C1 O1 C9 116.0(4) . . ?
C7 O2 Eu1 154.2(3) . 1_455 ?
C7 O2 Eu1 91.5(3) . 2_666 ?
Eu1 O2 Eu1 114.21(13) 1_455 2_666 ?
C7 O3 Eu1 96.6(3) . 2_666 ?
C8 O4 Eu1 92.4(3) . . ?
C8 O5 Eu1 93.1(3) . . ?
C15 O7 H7A 119.2 . . ?
C16 O8 Eu1 118.4(3) . . ?
C16 O9 Eu1 119.3(3) . 2_676 ?
Eu1 O10 H10A 124(4) . . ?
Eu1 O10 H10B 120(4) . . ?
H10A O10 H10B 116(5) . . ?
Eu1 O11 H11A 122(4) . . ?
Eu1 O11 H11B 124(4) . . ?
H11A O11 H11B 113(5) . . ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.174
####################################################################### 
# 
# 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 1422771'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O11 Sm'
_chemical_formula_weight         530.62

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   6.0004(3)
_cell_length_b                   9.8740(6)
_cell_length_c                   14.8700(8)
_cell_angle_alpha                85.714(2)
_cell_angle_beta                 89.557(2)
_cell_angle_gamma                74.826(2)
_cell_volume                     847.86(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3194
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      25.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.078
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    3.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7612
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.36
_diffrn_reflns_theta_max         25.94
_reflns_number_total             3194
_reflns_number_gt                2735
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0250P)²+2.7606P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3194
_refine_ls_number_parameters     253
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0751
_refine_ls_wR_factor_gt          0.0706
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.17483(5) 0.29288(3) 0.04200(2) 0.01024(10) Uani 1 1 d . . .
O1 O -0.0078(6) 0.6217(4) 0.2641(3) 0.0181(9) Uani 1 1 d . . .
O2 O 0.3839(6) 0.3102(4) -0.1023(2) 0.0140(9) Uani 1 1 d . . .
O3 O -0.1160(6) 0.4972(4) 0.0784(2) 0.0126(8) Uani 1 1 d . . .
O4 O 0.2870(7) 0.3033(4) 0.2007(3) 0.0162(9) Uani 1 1 d . . .
O5 O 0.4151(6) 0.4362(4) 0.0973(2) 0.0117(8) Uani 1 1 d . . .
O6 O 0.2499(8) 1.0843(5) 0.4399(3) 0.0309(11) Uani 1 1 d . . .
H6 H 0.3596 1.0918 0.4723 0.046 Uiso 1 1 calc R . .
O7 O 0.4363(7) 0.8562(5) 0.4600(3) 0.0258(10) Uani 1 1 d . . .
O8 O 0.2113(6) 0.0720(4) -0.0268(3) 0.0160(9) Uani 1 1 d . . .
O9 O 0.5504(6) 0.1250(4) 0.0696(3) 0.0148(9) Uani 1 1 d . . .
O10 O -0.0525(7) 0.1742(5) 0.1387(3) 0.0231(10) Uani 1 1 d . . .
H10A H -0.1352 0.1385 0.1064 0.035 Uiso 1 1 d R . .
H10C H 0.0375 0.1093 0.1720 0.035 Uiso 1 1 d R . .
O11 O -0.1516(6) 0.2955(4) -0.0519(3) 0.0198(9) Uani 1 1 d . . .
H11A H -0.1126 0.2307 -0.0880 0.030 Uiso 1 1 d R . .
H11B H -0.2611 0.2814 -0.0190 0.030 Uiso 1 1 d R . .
C1 C -0.1694(9) 0.5483(6) 0.2908(4) 0.0135(12) Uani 1 1 d . . .
C2 C -0.2986(9) 0.5122(6) 0.2229(4) 0.0132(12) Uani 1 1 d . . .
C3 C -0.4492(9) 0.4298(6) 0.2482(3) 0.0114(12) Uani 1 1 d . . .
C4 C -0.4687(10) 0.3871(6) 0.3381(4) 0.0188(13) Uani 1 1 d . . .
H4A H -0.5721 0.3316 0.3548 0.023 Uiso 1 1 calc R . .
C5 C -0.3388(10) 0.4246(6) 0.4038(4) 0.0207(14) Uani 1 1 d . . .
H5A H -0.3530 0.3947 0.4653 0.025 Uiso 1 1 calc R . .
C6 C -0.1883(11) 0.5058(7) 0.3800(4) 0.0234(15) Uani 1 1 d . . .
H6A H -0.0989 0.5319 0.4248 0.028 Uiso 1 1 calc R . .
C7 C -0.2693(9) 0.5697(6) 0.1288(3) 0.0105(11) Uani 1 1 d U . .
C8 C 0.4074(9) 0.3881(6) 0.1785(4) 0.0120(12) Uani 1 1 d . . .
C9 C -0.0462(10) 0.7575(6) 0.2937(4) 0.0176(13) Uani 1 1 d . . .
C10 C 0.1255(10) 0.7875(7) 0.3431(4) 0.0179(13) Uani 1 1 d . . .
H10B H 0.2637 0.7168 0.3584 0.021 Uiso 1 1 calc R . .
C11 C 0.0937(9) 0.9222(6) 0.3703(4) 0.0156(13) Uani 1 1 d . . .
C12 C -0.1074(10) 1.0273(7) 0.3465(4) 0.0196(13) Uani 1 1 d . . .
H12A H -0.1283 1.1201 0.3645 0.023 Uiso 1 1 calc R . .
C13 C -0.2759(10) 0.9929(7) 0.2961(4) 0.0192(14) Uani 1 1 d . . .
H13A H -0.4137 1.0633 0.2798 0.023 Uiso 1 1 calc R . .
C14 C -0.2473(10) 0.8597(7) 0.2693(4) 0.0195(14) Uani 1 1 d . . .
H14A H -0.3637 0.8377 0.2346 0.023 Uiso 1 1 calc R . .
C15 C 0.2743(10) 0.9542(7) 0.4267(4) 0.0208(14) Uani 1 1 d . . .
C16 C 0.4011(9) -0.0153(6) -0.0276(4) 0.0128(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
Sm1 O3 2.390(4) . ?
Sm1 O11 2.408(4) . ?
Sm1 O10 2.420(4) . ?
Sm1 O8 2.435(4) . ?
Sm1 O9 2.439(3) . ?
Sm1 O5 2.453(4) . ?
Sm1 O4 2.476(4) . ?
Sm1 O2 2.495(4) . ?
Sm1 O3 2.588(4) 2_565 ?
Sm1 C8 2.823(6) . ?
Sm1 C7 2.911(5) 2_565 ?
O1 C1 1.393(7) . ?
O1 C9 1.404(7) . ?
O2 C7 1.242(6) 2_565 ?
O3 C7 1.282(6) . ?
O3 Sm1 2.588(4) 2_565 ?
O4 C8 1.267(7) . ?
O5 C8 1.269(6) . ?
O6 C15 1.284(7) . ?
O6 H6 0.8400 . ?
O7 C15 1.254(7) . ?
O8 C16 1.236(6) . ?
O9 C16 1.257(7) 2_655 ?
O10 H10A 0.8500 . ?
O10 H10C 0.8500 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8499 . ?
C1 C6 1.373(8) . ?
C1 C2 1.400(8) . ?
C2 C3 1.397(8) . ?
C2 C7 1.498(7) . ?
C3 C4 1.384(7) . ?
C3 C8 1.499(8) 1_455 ?
C4 C5 1.384(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.384(9) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C7 O2 1.242(6) 2_565 ?
C7 Sm1 2.911(5) 2_565 ?
C8 C3 1.499(8) 1_655 ?
C9 C10 1.376(8) . ?
C9 C14 1.386(8) . ?
C10 C11 1.385(8) . ?
C10 H10B 0.9500 . ?
C11 C12 1.398(8) . ?
C11 C15 1.486(8) . ?
C12 C13 1.389(8) . ?
C12 H12A 0.9500 . ?
C13 C14 1.371(9) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C16 O9 1.257(7) 2_655 ?
C16 C16 1.553(11) 2_655 ?

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
O3 Sm1 O11 75.22(13) . . ?
O3 Sm1 O10 82.51(14) . . ?
O11 Sm1 O10 76.69(13) . . ?
O3 Sm1 O8 139.88(12) . . ?
O11 Sm1 O8 66.88(13) . . ?
O10 Sm1 O8 76.61(14) . . ?
O3 Sm1 O9 151.17(13) . . ?
O11 Sm1 O9 133.20(13) . . ?
O10 Sm1 O9 98.12(13) . . ?
O8 Sm1 O9 66.70(12) . . ?
O3 Sm1 O5 79.44(12) . . ?
O11 Sm1 O5 144.79(13) . . ?
O10 Sm1 O5 123.79(13) . . ?
O8 Sm1 O5 140.44(12) . . ?
O9 Sm1 O5 76.37(12) . . ?
O3 Sm1 O4 80.77(12) . . ?
O11 Sm1 O4 142.17(13) . . ?
O10 Sm1 O4 71.50(13) . . ?
O8 Sm1 O4 122.76(12) . . ?
O9 Sm1 O4 72.30(13) . . ?
O5 Sm1 O4 53.29(12) . . ?
O3 Sm1 O2 116.96(12) . . ?
O11 Sm1 O2 85.59(13) . . ?
O10 Sm1 O2 149.49(14) . . ?
O8 Sm1 O2 73.62(13) . . ?
O9 Sm1 O2 76.14(12) . . ?
O5 Sm1 O2 84.53(12) . . ?
O4 Sm1 O2 131.76(12) . . ?
O3 Sm1 O3 65.84(14) . 2_565 ?
O11 Sm1 O3 71.37(12) . 2_565 ?
O10 Sm1 O3 139.46(12) . 2_565 ?
O8 Sm1 O3 111.53(12) . 2_565 ?
O9 Sm1 O3 121.91(12) . 2_565 ?
O5 Sm1 O3 76.16(12) . 2_565 ?
O4 Sm1 O3 123.73(12) . 2_565 ?
O2 Sm1 O3 51.13(11) . 2_565 ?
O3 Sm1 C8 79.85(13) . . ?
O11 Sm1 C8 154.94(14) . . ?
O10 Sm1 C8 97.83(15) . . ?
O8 Sm1 C8 136.35(13) . . ?
O9 Sm1 C8 71.49(14) . . ?
O5 Sm1 C8 26.68(14) . . ?
O4 Sm1 C8 26.65(14) . . ?
O2 Sm1 C8 108.21(14) . . ?
O3 Sm1 C8 100.60(14) 2_565 . ?
O3 Sm1 C7 91.95(14) . 2_565 ?
O11 Sm1 C7 76.26(14) . 2_565 ?
O10 Sm1 C7 152.92(14) . 2_565 ?
O8 Sm1 C7 91.47(14) . 2_565 ?
O9 Sm1 C7 99.28(13) . 2_565 ?
O5 Sm1 C7 80.64(13) . 2_565 ?
O4 Sm1 C7 133.93(14) . 2_565 ?
O2 Sm1 C7 25.07(13) . 2_565 ?
O3 Sm1 C7 26.13(13) 2_565 2_565 ?
C8 Sm1 C7 107.30(15) . 2_565 ?
C1 O1 C9 116.0(4) . . ?
C7 O2 Sm1 96.6(3) 2_565 . ?
C7 O3 Sm1 154.6(3) . . ?
C7 O3 Sm1 91.2(3) . 2_565 ?
Sm1 O3 Sm1 114.16(14) . 2_565 ?
C8 O4 Sm1 92.1(3) . . ?
C8 O5 Sm1 93.1(3) . . ?
C15 O6 H6 109.5 . . ?
C16 O8 Sm1 119.9(3) . . ?
C16 O9 Sm1 118.5(3) 2_655 . ?
Sm1 O10 H10A 109.3 . . ?
Sm1 O10 H10C 109.3 . . ?
H10A O10 H10C 109.5 . . ?
Sm1 O11 H11A 109.3 . . ?
Sm1 O11 H11B 109.4 . . ?
H11A O11 H11B 109.5 . . ?
C6 C1 O1 120.6(5) . . ?
C6 C1 C2 121.9(6) . . ?
O1 C1 C2 117.3(5) . . ?
C1 C2 C3 117.9(5) . . ?
C1 C2 C7 116.8(5) . . ?
C3 C2 C7 125.3(5) . . ?
C4 C3 C2 120.2(5) . . ?
C4 C3 C8 119.4(5) . 1_455 ?
C2 C3 C8 120.3(5) . 1_455 ?
C5 C4 C3 120.5(6) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C4 C5 C6 120.0(5) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 119.4(5) . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
O2 C7 O3 120.9(5) 2_565 . ?
O2 C7 C2 119.7(5) 2_565 . ?
O3 C7 C2 119.3(5) . . ?
O2 C7 Sm1 58.4(3) 2_565 2_565 ?
O3 C7 Sm1 62.7(3) . 2_565 ?
C2 C7 Sm1 171.5(4) . 2_565 ?
O4 C8 O5 121.3(5) . . ?
O4 C8 C3 120.0(5) . 1_655 ?
O5 C8 C3 118.7(5) . 1_655 ?
O4 C8 Sm1 61.2(3) . . ?
O5 C8 Sm1 60.2(3) . . ?
C3 C8 Sm1 174.8(4) 1_655 . ?
C10 C9 C14 121.4(6) . . ?
C10 C9 O1 118.2(5) . . ?
C14 C9 O1 120.3(5) . . ?
C9 C10 C11 119.0(5) . . ?
C9 C10 H10B 120.5 . . ?
C11 C10 H10B 120.5 . . ?
C10 C11 C12 120.7(5) . . ?
C10 C11 C15 119.4(5) . . ?
C12 C11 C15 119.9(6) . . ?
C13 C12 C11 118.5(6) . . ?
C13 C12 H12A 120.7 . . ?
C11 C12 H12A 120.7 . . ?
C14 C13 C12 121.4(6) . . ?
C14 C13 H13A 119.3 . . ?
C12 C13 H13A 119.3 . . ?
C13 C14 C9 119.0(6) . . ?
C13 C14 H14A 120.5 . . ?
C9 C14 H14A 120.5 . . ?
O7 C15 O6 123.6(6) . . ?
O7 C15 C11 120.0(6) . . ?
O6 C15 C11 116.5(5) . . ?
O8 C16 O9 126.3(5) . 2_655 ?
O8 C16 C16 116.5(6) . 2_655 ?
O9 C16 C16 117.2(6) 2_655 2_655 ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        25.94
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         1.041
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.187
####################################################################### 
# 
# 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 1422772'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Gd O11'
_chemical_formula_weight         537.51

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   5.9892(19)
_cell_length_b                   9.875(3)
_cell_length_c                   14.943(5)
_cell_angle_alpha                85.973(11)
_cell_angle_beta                 89.739(12)
_cell_angle_gamma                74.765(10)
_cell_volume                     850.5(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    284(2)
_cell_measurement_reflns_used    3034
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      25.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.099
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    3.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      284(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6995
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_sigmaI/netI    0.0812
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         25.47
_reflns_number_total             3034
_reflns_number_gt                2487
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0320P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3034
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
Gd1 Gd 0.82409(6) 0.70776(3) 0.45939(2) 0.01645(11) Uani 1 1 d . . .
O1 O 0.0065(8) 0.3797(5) 0.2367(3) 0.0275(11) Uani 1 1 d . . .
O2 O 0.6189(7) 0.6877(4) 0.6006(3) 0.0218(11) Uani 1 1 d . . .
O3 O 1.1142(7) 0.5045(4) 0.4219(3) 0.0222(11) Uani 1 1 d . . .
O4 O 0.5831(7) 0.5658(4) 0.4046(3) 0.0209(10) Uani 1 1 d . . .
O5 O 0.7147(8) 0.6960(5) 0.3016(3) 0.0262(11) Uani 1 1 d . . .
O6 O -0.4369(10) 0.1444(5) 0.0406(4) 0.0410(14) Uani 1 1 d . . .
O7 O -0.2493(10) -0.0838(5) 0.0603(4) 0.0510(17) Uani 1 1 d . . .
H7 H -0.3553 -0.0906 0.0278 0.076 Uiso 1 1 calc R . .
O8 O 0.7886(7) 0.9270(4) 0.5286(3) 0.0283(12) Uani 1 1 d . . .
O9 O 0.4517(7) 0.8742(4) 0.4313(3) 0.0255(11) Uani 1 1 d . . .
O10 O 1.1495(8) 0.7046(5) 0.5516(3) 0.0313(12) Uani 1 1 d . . .
H10A H 1.2394 0.7445 0.5223 0.047 Uiso 1 1 d R . .
H10C H 1.1031 0.7486 0.5979 0.047 Uiso 1 1 d R . .
O11 O 1.0427(9) 0.8302(6) 0.3641(3) 0.0435(14) Uani 1 1 d . . .
H11A H 0.9783 0.8492 0.3125 0.065 Uiso 1 1 d R . .
H11B H 1.0460 0.9062 0.3869 0.065 Uiso 1 1 d R . .
C1 C 0.1701(11) 0.4525(6) 0.2110(4) 0.0212(15) Uani 1 1 d . . .
C2 C 0.2973(11) 0.4898(6) 0.2787(4) 0.0184(15) Uani 1 1 d . . .
C3 C 0.4511(11) 0.5708(6) 0.2536(4) 0.0198(15) Uani 1 1 d . . .
C4 C 0.4704(12) 0.6131(7) 0.1639(4) 0.0257(16) Uani 1 1 d . . .
H4A H 0.5717 0.6673 0.1477 0.031 Uiso 1 1 calc R . .
C5 C 0.3414(14) 0.5757(8) 0.0988(5) 0.0355(19) Uani 1 1 d . . .
H5A H 0.3558 0.6052 0.0390 0.043 Uiso 1 1 calc R . .
C6 C 0.1906(14) 0.4948(8) 0.1211(5) 0.037(2) Uani 1 1 d . . .
H6A H 0.1042 0.4689 0.0770 0.044 Uiso 1 1 calc R . .
C7 C 0.7342(10) 0.5665(6) 0.6267(4) 0.0175(14) Uani 1 1 d . . .
C8 C 0.5911(11) 0.6128(6) 0.3238(4) 0.0190(15) Uani 1 1 d . . .
C9 C 0.0451(12) 0.2447(7) 0.2069(5) 0.0275(17) Uani 1 1 d . . .
C10 C -0.1249(12) 0.2146(7) 0.1579(4) 0.0274(17) Uani 1 1 d . . .
H10B H -0.2593 0.2844 0.1422 0.033 Uiso 1 1 calc R . .
C11 C -0.0959(12) 0.0781(7) 0.1312(5) 0.0270(17) Uani 1 1 d . . .
C12 C 0.1048(13) -0.0251(7) 0.1560(5) 0.0337(19) Uani 1 1 d . . .
H12A H 0.1249 -0.1160 0.1386 0.040 Uiso 1 1 calc R . .
C13 C 0.2737(13) 0.0065(8) 0.2061(5) 0.0325(18) Uani 1 1 d . . .
H13A H 0.4074 -0.0632 0.2228 0.039 Uiso 1 1 calc R . .
C14 C 0.2448(13) 0.1428(8) 0.2320(5) 0.0331(18) Uani 1 1 d . . .
H14A H 0.3588 0.1649 0.2657 0.040 Uiso 1 1 calc R . .
C15 C -0.2736(13) 0.0456(7) 0.0742(5) 0.0294(17) Uani 1 1 d . . .
C16 C 0.5986(11) 1.0143(6) 0.5278(4) 0.0190(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
Gd1 O3 2.383(4) . ?
Gd1 O10 2.384(4) . ?
Gd1 O11 2.404(5) . ?
Gd1 O9 2.416(4) . ?
Gd1 O8 2.423(4) . ?
Gd1 O4 2.439(4) . ?
Gd1 O2 2.459(5) . ?
Gd1 O5 2.468(4) . ?
Gd1 O3 2.598(4) 2_766 ?
Gd1 C8 2.813(6) . ?
Gd1 C7 2.894(7) . ?
O1 C9 1.396(8) . ?
O1 C1 1.397(8) . ?
O2 C7 1.250(7) . ?
O3 C7 1.255(7) 2_766 ?
O3 Gd1 2.598(4) 2_766 ?
O4 C8 1.268(8) . ?
O5 C8 1.270(8) . ?
O6 C15 1.263(8) . ?
O7 C15 1.279(8) . ?
O7 H7 0.8200 . ?
O8 C16 1.234(7) . ?
O9 C16 1.262(7) 2_676 ?
O10 H10A 0.8500 . ?
O10 H10C 0.8500 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8501 . ?
C1 C6 1.393(10) . ?
C1 C2 1.395(8) . ?
C2 C3 1.404(9) . ?
C2 C7 1.512(9) 2_666 ?
C3 C4 1.390(9) . ?
C3 C8 1.492(8) . ?
C4 C5 1.374(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.380(11) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 O3 1.255(7) 2_766 ?
C7 C2 1.512(9) 2_666 ?
C9 C10 1.363(9) . ?
C9 C14 1.379(9) . ?
C10 C11 1.399(9) . ?
C10 H10B 0.9300 . ?
C11 C12 1.388(9) . ?
C11 C15 1.479(9) . ?
C12 C13 1.373(10) . ?
C12 H12A 0.9300 . ?
C13 C14 1.393(10) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C16 O9 1.262(7) 2_676 ?
C16 C16 1.544(12) 2_676 ?

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
O3 Gd1 O10 75.23(15) . . ?
O3 Gd1 O11 83.54(18) . . ?
O10 Gd1 O11 77.12(17) . . ?
O3 Gd1 O9 150.63(15) . . ?
O10 Gd1 O9 133.61(15) . . ?
O11 Gd1 O9 96.59(18) . . ?
O3 Gd1 O8 139.89(15) . . ?
O10 Gd1 O8 66.89(14) . . ?
O11 Gd1 O8 75.84(18) . . ?
O9 Gd1 O8 67.02(14) . . ?
O3 Gd1 O4 79.57(15) . . ?
O10 Gd1 O4 144.79(15) . . ?
O11 Gd1 O4 124.08(16) . . ?
O9 Gd1 O4 76.13(14) . . ?
O8 Gd1 O4 140.30(15) . . ?
O3 Gd1 O2 116.68(14) . . ?
O10 Gd1 O2 85.96(16) . . ?
O11 Gd1 O2 149.48(17) . . ?
O9 Gd1 O2 76.90(15) . . ?
O8 Gd1 O2 74.19(16) . . ?
O4 Gd1 O2 83.80(15) . . ?
O3 Gd1 O5 79.95(14) . . ?
O10 Gd1 O5 141.51(17) . . ?
O11 Gd1 O5 71.20(16) . . ?
O9 Gd1 O5 72.44(15) . . ?
O8 Gd1 O5 123.28(15) . . ?
O4 Gd1 O5 53.54(15) . . ?
O2 Gd1 O5 131.88(15) . . ?
O3 Gd1 O3 65.68(17) . 2_766 ?
O10 Gd1 O3 71.51(15) . 2_766 ?
O11 Gd1 O3 140.39(16) . 2_766 ?
O9 Gd1 O3 122.54(15) . 2_766 ?
O8 Gd1 O3 111.79(15) . 2_766 ?
O4 Gd1 O3 75.90(14) . 2_766 ?
O2 Gd1 O3 51.02(13) . 2_766 ?
O5 Gd1 O3 123.16(14) . 2_766 ?
O3 Gd1 C8 79.59(15) . . ?
O10 Gd1 C8 154.71(16) . . ?
O11 Gd1 C8 97.86(19) . . ?
O9 Gd1 C8 71.27(15) . . ?
O8 Gd1 C8 136.58(15) . . ?
O4 Gd1 C8 26.75(17) . . ?
O2 Gd1 C8 107.77(18) . . ?
O5 Gd1 C8 26.83(17) . . ?
O3 Gd1 C8 100.24(17) 2_766 . ?
O3 Gd1 C7 91.37(17) . . ?
O10 Gd1 C7 76.54(17) . . ?
O11 Gd1 C7 153.61(17) . . ?
O9 Gd1 C7 100.29(17) . . ?
O8 Gd1 C7 92.25(17) . . ?
O4 Gd1 C7 79.94(16) . . ?
O2 Gd1 C7 25.38(14) . . ?
O5 Gd1 C7 133.46(17) . . ?
O3 Gd1 C7 25.69(14) 2_766 . ?
C8 Gd1 C7 106.69(19) . . ?
C9 O1 C1 115.9(5) . . ?
C7 O2 Gd1 97.2(4) . . ?
C7 O3 Gd1 155.2(4) 2_766 . ?
C7 O3 Gd1 90.5(4) 2_766 2_766 ?
Gd1 O3 Gd1 114.32(17) . 2_766 ?
C8 O4 Gd1 93.3(4) . . ?
C8 O5 Gd1 91.9(4) . . ?
C15 O7 H7 109.5 . . ?
C16 O8 Gd1 119.2(4) . . ?
C16 O9 Gd1 119.1(4) 2_676 . ?
Gd1 O10 H10A 109.3 . . ?
Gd1 O10 H10C 109.3 . . ?
H10A O10 H10C 109.5 . . ?
Gd1 O11 H11A 109.3 . . ?
Gd1 O11 H11B 109.1 . . ?
H11A O11 H11B 109.5 . . ?
O1 C1 C6 120.2(6) . . ?
O1 C1 C2 117.7(6) . . ?
C6 C1 C2 121.8(7) . . ?
C1 C2 C3 117.9(6) . . ?
C1 C2 C7 116.9(6) . 2_666 ?
C3 C2 C7 125.2(5) . 2_666 ?
C4 C3 C2 120.0(6) . . ?
C4 C3 C8 120.2(6) . . ?
C2 C3 C8 119.7(6) . . ?
C5 C4 C3 120.7(7) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C5 C6 C1 118.8(6) . . ?
C5 C6 H6A 120.6 . . ?
C1 C6 H6A 120.6 . . ?
O2 C7 O3 121.1(6) . 2_766 ?
O2 C7 C2 118.9(5) . 2_666 ?
O3 C7 C2 119.7(5) 2_766 2_666 ?
O2 C7 Gd1 57.4(3) . . ?
O3 C7 Gd1 63.9(3) 2_766 . ?
C2 C7 Gd1 170.6(4) 2_666 . ?
O5 C8 O4 121.1(6) . . ?
O5 C8 C3 119.4(6) . . ?
O4 C8 C3 119.5(6) . . ?
O5 C8 Gd1 61.3(3) . . ?
O4 C8 Gd1 60.0(3) . . ?
C3 C8 Gd1 175.6(4) . . ?
C10 C9 C14 121.4(6) . . ?
C10 C9 O1 118.4(6) . . ?
C14 C9 O1 120.1(6) . . ?
C9 C10 C11 119.6(6) . . ?
C9 C10 H10B 120.2 . . ?
C11 C10 H10B 120.2 . . ?
C12 C11 C10 119.4(6) . . ?
C12 C11 C15 120.4(6) . . ?
C10 C11 C15 120.2(6) . . ?
C13 C12 C11 120.4(7) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C14 120.0(6) . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C9 C14 C13 119.2(6) . . ?
C9 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
O6 C15 O7 123.3(6) . . ?
O6 C15 C11 119.7(6) . . ?
O7 C15 C11 117.0(6) . . ?
O8 C16 O9 126.3(6) . 2_676 ?
O8 C16 C16 117.5(7) . 2_676 ?
O9 C16 C16 116.2(6) 2_676 2_676 ?

_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_theta_full        25.47
_diffrn_measured_fraction_theta_full 0.962
_refine_diff_density_max         0.812
_refine_diff_density_min         -1.331
_refine_diff_density_rms         0.172
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1422773'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O11 Tb'
_chemical_formula_weight         539.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   6.017(6)
_cell_length_b                   9.899(9)
_cell_length_c                   14.985(14)
_cell_angle_alpha                85.785(11)
_cell_angle_beta                 89.875(10)
_cell_angle_gamma                74.800(10)
_cell_volume                     858.9(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3254
_cell_measurement_theta_min      1.36
_cell_measurement_theta_max      26.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.085
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             522
_exptl_absorpt_coefficient_mu    4.180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6357
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         26.93
_reflns_number_total             3254
_reflns_number_gt                2894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0441P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3254
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 0.82348(4) 0.70802(3) -0.040140(18) 0.01798(11) Uani 1 1 d . . .
O1 O 0.9917(7) 0.6204(5) 0.2635(3) 0.0296(10) Uani 1 1 d . . .
O2 O 0.6211(6) 0.6866(4) 0.0998(3) 0.0218(9) Uani 1 1 d . . .
O3 O 0.8872(6) 0.4929(4) 0.0786(3) 0.0230(9) Uani 1 1 d . . .
O4 O 0.5840(6) 0.5662(4) -0.0941(3) 0.0202(9) Uani 1 1 d . . .
O5 O 0.7160(7) 0.6972(4) -0.1974(3) 0.0273(10) Uani 1 1 d . . .
O6 O 1.2480(9) 1.0834(5) 0.4395(4) 0.0512(14) Uani 1 1 d . . .
H6 H 1.3539 1.0918 0.4711 0.077 Uiso 1 1 calc R . .
O7 O 1.4380(8) 0.8550(5) 0.4597(3) 0.0432(12) Uani 1 1 d . . .
O8 O 0.7894(7) 0.9264(4) 0.0291(3) 0.0305(10) Uani 1 1 d . . .
O9 O 0.4518(6) 0.8734(4) -0.0679(3) 0.0246(9) Uani 1 1 d . . .
O10 O 1.0363(9) 0.8305(6) -0.1347(3) 0.0468(14) Uani 1 1 d . . .
H10A H 0.9715 0.8494 -0.1861 0.070 Uiso 1 1 d R . .
H10C H 1.0395 0.9064 -0.1122 0.070 Uiso 1 1 d R . .
O11 O 1.1489(7) 0.7025(5) 0.0514(3) 0.0318(10) Uani 1 1 d . . .
H11A H 1.2389 0.7420 0.0222 0.048 Uiso 1 1 d R . .
H11B H 1.1037 0.7460 0.0977 0.048 Uiso 1 1 d R . .
C1 C 0.8294(10) 0.5457(6) 0.2885(4) 0.0240(13) Uani 1 1 d . . .
C2 C 0.7040(9) 0.5107(6) 0.2207(4) 0.0205(12) Uani 1 1 d . . .
C3 C 0.5500(9) 0.4290(6) 0.2447(4) 0.0198(12) Uiso 1 1 d . . .
C4 C 0.5260(10) 0.3853(6) 0.3355(4) 0.0245(13) Uani 1 1 d . . .
H4A H 0.4236 0.3321 0.3512 0.029 Uiso 1 1 calc R . .
C5 C 0.6572(12) 0.4231(7) 0.4008(4) 0.0357(16) Uani 1 1 d . . .
H5A H 0.6455 0.3926 0.4604 0.043 Uiso 1 1 calc R . .
C6 C 0.8060(12) 0.5062(7) 0.3779(4) 0.0359(17) Uani 1 1 d . . .
H6A H 0.8885 0.5347 0.4219 0.043 Uiso 1 1 calc R . .
C7 C 0.7337(9) 0.5668(6) 0.1261(4) 0.0185(12) Uani 1 1 d . . .
C8 C 0.5956(9) 0.6155(6) -0.1751(4) 0.0200(13) Uani 1 1 d . . .
C9 C 0.9529(11) 0.7561(7) 0.2925(4) 0.0298(15) Uani 1 1 d . . .
C10 C 1.1264(10) 0.7850(7) 0.3421(4) 0.0267(14) Uani 1 1 d . . .
H10B H 1.2608 0.7154 0.3572 0.032 Uiso 1 1 calc R . .
C11 C 1.0960(11) 0.9206(7) 0.3692(4) 0.0319(15) Uani 1 1 d . . .
C12 C 0.8979(12) 1.0253(7) 0.3433(4) 0.0344(16) Uani 1 1 d . . .
H12A H 0.8805 1.1166 0.3591 0.041 Uiso 1 1 calc R . .
C13 C 0.7258(12) 0.9928(7) 0.2935(4) 0.0364(16) Uani 1 1 d . . .
H13A H 0.5913 1.0618 0.2778 0.044 Uiso 1 1 calc R . .
C14 C 0.7543(11) 0.8592(8) 0.2677(4) 0.0352(16) Uani 1 1 d . . .
H14A H 0.6405 0.8380 0.2337 0.042 Uiso 1 1 calc R . .
C15 C 1.2764(12) 0.9531(7) 0.4261(4) 0.0326(15) Uani 1 1 d . . .
C16 C 0.5993(9) 1.0141(6) 0.0282(4) 0.0198(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
Tb1 O11 2.379(4) . ?
Tb1 O10 2.381(5) . ?
Tb1 O3 2.380(4) 2_765 ?
Tb1 O9 2.416(4) . ?
Tb1 O8 2.426(4) . ?
Tb1 O4 2.436(4) . ?
Tb1 O2 2.446(4) . ?
Tb1 O5 2.462(5) . ?
Tb1 O3 2.620(4) . ?
Tb1 C8 2.784(6) . ?
Tb1 C7 2.887(6) . ?
O1 C9 1.404(7) . ?
O1 C1 1.406(7) . ?
O2 C7 1.238(7) . ?
O3 C7 1.271(6) . ?
O3 Tb1 2.380(4) 2_765 ?
O4 C8 1.284(7) . ?
O5 C8 1.248(7) . ?
O6 C15 1.287(8) . ?
O6 H6 0.8200 . ?
O7 C15 1.255(8) . ?
O8 C16 1.241(7) . ?
O9 C16 1.267(7) 2_675 ?
O10 H10A 0.8500 . ?
O10 H10C 0.8500 . ?
O11 H11A 0.8500 . ?
O11 H11B 0.8500 . ?
C1 C6 1.385(9) . ?
C1 C2 1.383(8) . ?
C2 C3 1.411(8) . ?
C2 C7 1.511(8) . ?
C3 C4 1.416(8) . ?
C3 C8 1.524(8) 2_665 ?
C4 C5 1.391(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.393(10) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C8 C3 1.524(8) 2_665 ?
C9 C10 1.384(8) . ?
C9 C14 1.383(9) . ?
C10 C11 1.397(9) . ?
C10 H10B 0.9300 . ?
C11 C12 1.393(10) . ?
C11 C15 1.496(9) . ?
C12 C13 1.395(9) . ?
C12 H12A 0.9300 . ?
C13 C14 1.372(10) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C16 O9 1.267(7) 2_675 ?
C16 C16 1.560(11) 2_675 ?

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
O11 Tb1 O10 77.48(17) . . ?
O11 Tb1 O3 74.78(15) . 2_765 ?
O10 Tb1 O3 83.23(18) . 2_765 ?
O11 Tb1 O9 134.19(15) . . ?
O10 Tb1 O9 96.52(18) . . ?
O3 Tb1 O9 150.47(14) 2_765 . ?
O11 Tb1 O8 67.25(14) . . ?
O10 Tb1 O8 75.77(17) . . ?
O3 Tb1 O8 139.61(13) 2_765 . ?
O9 Tb1 O8 67.27(13) . . ?
O11 Tb1 O4 144.16(14) . . ?
O10 Tb1 O4 124.15(15) . . ?
O3 Tb1 O4 79.71(15) 2_765 . ?
O9 Tb1 O4 76.09(14) . . ?
O8 Tb1 O4 140.45(13) . . ?
O11 Tb1 O2 86.19(16) . . ?
O10 Tb1 O2 149.65(16) . . ?
O3 Tb1 O2 117.13(13) 2_765 . ?
O9 Tb1 O2 76.73(14) . . ?
O8 Tb1 O2 74.35(15) . . ?
O4 Tb1 O2 83.46(14) . . ?
O11 Tb1 O5 140.97(15) . . ?
O10 Tb1 O5 70.73(15) . . ?
O3 Tb1 O5 79.44(14) 2_765 . ?
O9 Tb1 O5 72.73(14) . . ?
O8 Tb1 O5 123.39(15) . . ?
O4 Tb1 O5 54.03(13) . . ?
O2 Tb1 O5 132.09(14) . . ?
O11 Tb1 O3 71.33(14) . . ?
O10 Tb1 O3 140.59(16) . . ?
O3 Tb1 O3 65.94(15) 2_765 . ?
O9 Tb1 O3 122.48(13) . . ?
O8 Tb1 O3 112.03(15) . . ?
O4 Tb1 O3 75.47(13) . . ?
O2 Tb1 O3 51.21(12) . . ?
O5 Tb1 O3 122.97(14) . . ?
O11 Tb1 C8 154.01(15) . . ?
O10 Tb1 C8 97.20(18) . . ?
O3 Tb1 C8 79.35(15) 2_765 . ?
O9 Tb1 C8 71.36(15) . . ?
O8 Tb1 C8 136.72(15) . . ?
O4 Tb1 C8 27.45(15) . . ?
O2 Tb1 C8 108.12(17) . . ?
O5 Tb1 C8 26.61(15) . . ?
O3 Tb1 C8 100.34(16) . . ?
O11 Tb1 C7 76.66(15) . . ?
O10 Tb1 C7 154.06(15) . . ?
O3 Tb1 C7 92.06(15) 2_765 . ?
O9 Tb1 C7 99.88(15) . . ?
O8 Tb1 C7 92.21(17) . . ?
O4 Tb1 C7 79.56(14) . . ?
O2 Tb1 C7 25.14(14) . . ?
O5 Tb1 C7 133.56(15) . . ?
O3 Tb1 C7 26.12(13) . . ?
C8 Tb1 C7 107.01(17) . . ?
C9 O1 C1 116.8(5) . . ?
C7 O2 Tb1 97.8(3) . . ?
C7 O3 Tb1 157.2(4) . 2_765 ?
C7 O3 Tb1 88.7(3) . . ?
Tb1 O3 Tb1 114.06(15) 2_765 . ?
C8 O4 Tb1 91.6(3) . . ?
C8 O5 Tb1 91.2(3) . . ?
C15 O6 H6 109.5 . . ?
C16 O8 Tb1 119.1(4) . . ?
C16 O9 Tb1 119.6(3) 2_675 . ?
Tb1 O10 H10A 109.3 . . ?
Tb1 O10 H10C 109.3 . . ?
H10A O10 H10C 109.5 . . ?
Tb1 O11 H11A 109.5 . . ?
Tb1 O11 H11B 109.2 . . ?
H11A O11 H11B 109.5 . . ?
C6 C1 C2 122.7(6) . . ?
C6 C1 O1 119.9(5) . . ?
C2 C1 O1 117.4(5) . . ?
C1 C2 C3 117.8(5) . . ?
C1 C2 C7 118.1(5) . . ?
C3 C2 C7 124.1(5) . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 C8 122.0(5) . 2_665 ?
C4 C3 C8 117.5(5) . 2_665 ?
C5 C4 C3 119.2(6) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 120.6(6) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 119.1(6) . . ?
C1 C6 H6A 120.4 . . ?
C5 C6 H6A 120.4 . . ?
O2 C7 O3 122.1(5) . . ?
O2 C7 C2 119.3(5) . . ?
O3 C7 C2 118.4(5) . . ?
O2 C7 Tb1 57.1(3) . . ?
O3 C7 Tb1 65.1(3) . . ?
C2 C7 Tb1 170.2(4) . . ?
O5 C8 O4 123.0(5) . . ?
O5 C8 C3 120.5(5) . 2_665 ?
O4 C8 C3 116.5(5) . 2_665 ?
O5 C8 Tb1 62.1(3) . . ?
O4 C8 Tb1 61.0(3) . . ?
C3 C8 Tb1 174.6(4) 2_665 . ?
C10 C9 C14 121.4(6) . . ?
C10 C9 O1 117.5(6) . . ?
C14 C9 O1 121.0(6) . . ?
C9 C10 C11 118.8(6) . . ?
C9 C10 H10B 120.6 . . ?
C11 C10 H10B 120.6 . . ?
C10 C11 C12 120.1(6) . . ?
C10 C11 C15 119.9(6) . . ?
C12 C11 C15 120.1(6) . . ?
C11 C12 C13 119.7(6) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C14 C13 C12 120.2(6) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C9 119.8(6) . . ?
C13 C14 H14A 120.1 . . ?
C9 C14 H14A 120.1 . . ?
O7 C15 O6 124.4(6) . . ?
O7 C15 C11 119.8(6) . . ?
O6 C15 C11 115.8(6) . . ?
O8 C16 O9 126.8(5) . 2_675 ?
O8 C16 C16 117.6(6) . 2_675 ?
O9 C16 C16 115.6(6) 2_675 2_675 ?

_diffrn_measured_fraction_theta_max 0.875
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.945
_refine_diff_density_min         -0.912
_refine_diff_density_rms         0.166
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1422774'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Eu O9.50'
_chemical_formula_weight         496.21

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

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

_cell_length_a                   6.0112(9)
_cell_length_b                   11.419(2)
_cell_length_c                   12.2303(19)
_cell_angle_alpha                92.275(5)
_cell_angle_beta                 99.843(4)
_cell_angle_gamma                96.506(5)
_cell_volume                     820.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    2932
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      25.43

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.009
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             482
_exptl_absorpt_coefficient_mu    3.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      300(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6665
_diffrn_reflns_av_R_equivalents  0.1138
_diffrn_reflns_av_sigmaI/netI    0.1483
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         25.43
_reflns_number_total             2932
_reflns_number_gt                2039
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2932
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1545
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_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 0.58103(12) 0.13283(7) 0.89344(6) 0.0220(3) Uani 1 1 d . . .
OW1 O 0.5000 0.5000 1.0000 0.089(8) Uani 1 2 d S . .
HW1A H 0.4493 0.4998 1.0607 0.133 Uiso 0.50 1 d PR . .
HW1C H 0.4071 0.5279 0.9503 0.133 Uiso 0.50 1 d PR . .
O1 O 0.6650(16) 0.2245(9) 0.2956(7) 0.030(2) Uani 1 1 d . . .
O2 O 0.8737(17) 0.2356(10) 0.7964(8) 0.035(3) Uani 1 1 d . . .
O3 O 0.5381(16) 0.1788(10) 0.6950(8) 0.039(3) Uani 1 1 d . . .
O4 O 0.2707(17) 0.0305(9) 0.1999(8) 0.031(2) Uani 1 1 d . . .
O5 O 0.4230(15) 0.0876(9) 0.0590(7) 0.024(2) Uani 1 1 d . . .
O6 O -0.0690(15) 0.1340(8) 0.0278(8) 0.025(2) Uani 1 1 d . . .
O7 O -0.2174(16) 0.3021(9) 0.0161(8) 0.032(2) Uani 1 1 d . . .
O8 O 0.3263(16) 0.2829(9) 0.8856(8) 0.031(2) Uani 1 1 d . . .
H8B H 0.4032 0.3508 0.8916 0.046 Uiso 1 1 d R . .
H8C H 0.2356 0.2742 0.8236 0.046 Uiso 1 1 d R . .
O9 O 0.2155(17) 0.0315(10) 0.8117(9) 0.041(3) Uani 1 1 d . . .
H9A H 0.1508 0.0016 0.8625 0.062 Uiso 1 1 d R . .
H9B H 0.1344 0.0802 0.7786 0.062 Uiso 1 1 d R . .
C1 C 0.794(3) 0.2573(13) 0.4035(11) 0.029(3) Uani 1 1 d . . .
C2 C 0.702(2) 0.2304(13) 0.4962(11) 0.028(3) Uani 1 1 d . . .
H2A H 0.5526 0.1958 0.4898 0.034 Uiso 1 1 calc R . .
C3 C 0.838(2) 0.2561(14) 0.5989(10) 0.027(3) Uani 1 1 d . . .
C4 C 1.056(2) 0.3085(15) 0.6089(12) 0.035(4) Uani 1 1 d . . .
H4A H 1.1433 0.3281 0.6790 0.041 Uiso 1 1 calc R . .
C5 C 1.146(3) 0.3325(15) 0.5150(12) 0.036(4) Uani 1 1 d . . .
H5A H 1.2964 0.3653 0.5212 0.043 Uiso 1 1 calc R . .
C6 C 1.013(2) 0.3079(14) 0.4122(12) 0.031(4) Uani 1 1 d . . .
H6A H 1.0721 0.3258 0.3486 0.037 Uiso 1 1 calc R . .
C7 C 0.501(2) 0.2931(14) 0.2557(10) 0.027(3) Uani 1 1 d . . .
C8 C 0.324(2) 0.2382(12) 0.1748(11) 0.023(3) Uani 1 1 d . . .
C9 C 0.148(2) 0.3033(13) 0.1313(11) 0.025(3) Uani 1 1 d . . .
C10 C 0.156(2) 0.4213(12) 0.1649(11) 0.025(3) Uani 1 1 d . . .
H10A H 0.0396 0.4649 0.1367 0.030 Uiso 1 1 calc R . .
C11 C 0.346(3) 0.4742(14) 0.2430(12) 0.036(4) Uani 1 1 d . . .
H11A H 0.3559 0.5542 0.2633 0.043 Uiso 1 1 calc R . .
C12 C 0.511(3) 0.4132(13) 0.2886(12) 0.031(3) Uani 1 1 d . . .
H12A H 0.6319 0.4498 0.3413 0.037 Uiso 1 1 calc R . .
C13 C 0.743(2) 0.2198(13) 0.7015(12) 0.027(3) Uani 1 1 d . . .
C14 C 0.333(2) 0.1119(13) 0.1394(11) 0.023(3) Uani 1 1 d . . .
C15 C -0.060(2) 0.2437(12) 0.0541(11) 0.023(3) 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 O9 2.397(10) . ?
Eu1 O8 2.418(9) . ?
Eu1 O5 2.428(8) 1_556 ?
Eu1 O6 2.437(9) 1_656 ?
Eu1 O7 2.464(10) 1_656 ?
Eu1 O4 2.476(10) 2_656 ?
Eu1 O3 2.480(10) . ?
Eu1 O2 2.498(9) . ?
Eu1 O5 2.604(10) 2_656 ?
Eu1 C15 2.802(13) 1_656 ?
Eu1 C13 2.863(14) . ?
Eu1 C14 2.924(15) 2_656 ?
Eu1 H9A 2.7965 . ?
Eu1 H9B 2.7960 . ?
OW1 HW1A 0.8500 . ?
OW1 HW1C 0.8500 . ?
O1 C7 1.365(17) . ?
O1 C1 1.425(16) . ?
O2 C13 1.279(17) . ?
O3 C13 1.257(17) . ?
O4 C14 1.274(16) . ?
O4 Eu1 2.476(10) 2_656 ?
O5 C14 1.238(15) . ?
O5 Eu1 2.428(8) 1_554 ?
O5 Eu1 2.604(10) 2_656 ?
O6 C15 1.274(16) . ?
O6 Eu1 2.437(9) 1_454 ?
O7 C15 1.253(17) . ?
O7 Eu1 2.464(10) 1_454 ?
O8 H8B 0.8500 . ?
O8 H8C 0.8500 . ?
O9 H9A 0.8499 . ?
O9 H9B 0.8501 . ?
C1 C6 1.36(2) . ?
C1 C2 1.375(18) . ?
C2 C3 1.378(19) . ?
C2 H2A 0.9300 . ?
C3 C4 1.357(19) . ?
C3 C13 1.518(18) . ?
C4 C5 1.376(19) . ?
C4 H4A 0.9300 . ?
C5 C6 1.37(2) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.397(19) . ?
C7 C12 1.41(2) . ?
C8 C9 1.40(2) . ?
C8 C14 1.50(2) . ?
C9 C10 1.39(2) . ?
C9 C15 1.506(19) . ?
C10 C11 1.42(2) . ?
C10 H10A 0.9300 . ?
C11 C12 1.33(2) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C14 Eu1 2.924(15) 2_656 ?
C15 Eu1 2.802(13) 1_454 ?

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
O9 Eu1 O8 75.3(4) . . ?
O9 Eu1 O5 79.3(3) . 1_556 ?
O8 Eu1 O5 81.7(3) . 1_556 ?
O9 Eu1 O6 147.9(4) . 1_656 ?
O8 Eu1 O6 125.4(3) . 1_656 ?
O5 Eu1 O6 80.1(3) 1_556 1_656 ?
O9 Eu1 O7 145.1(4) . 1_656 ?
O8 Eu1 O7 73.1(3) . 1_656 ?
O5 Eu1 O7 81.7(3) 1_556 1_656 ?
O6 Eu1 O7 53.5(3) 1_656 1_656 ?
O9 Eu1 O4 84.3(4) . 2_656 ?
O8 Eu1 O4 149.5(3) . 2_656 ?
O5 Eu1 O4 116.8(3) 1_556 2_656 ?
O6 Eu1 O4 83.3(3) 1_656 2_656 ?
O7 Eu1 O4 130.6(3) 1_656 2_656 ?
O9 Eu1 O3 76.0(3) . . ?
O8 Eu1 O3 78.5(4) . . ?
O5 Eu1 O3 151.5(3) 1_556 . ?
O6 Eu1 O3 128.2(3) 1_656 . ?
O7 Eu1 O3 111.4(4) 1_656 . ?
O4 Eu1 O3 74.7(4) 2_656 . ?
O9 Eu1 O2 127.8(3) . . ?
O8 Eu1 O2 98.6(4) . . ?
O5 Eu1 O2 152.3(3) 1_556 . ?
O6 Eu1 O2 77.3(3) 1_656 . ?
O7 Eu1 O2 72.1(3) 1_656 . ?
O4 Eu1 O2 76.2(3) 2_656 . ?
O3 Eu1 O2 52.3(3) . . ?
O9 Eu1 O5 72.3(3) . 2_656 ?
O8 Eu1 O5 137.7(3) . 2_656 ?
O5 Eu1 O5 66.2(3) 1_556 2_656 ?
O6 Eu1 O5 76.9(3) 1_656 2_656 ?
O7 Eu1 O5 125.0(3) 1_656 2_656 ?
O4 Eu1 O5 50.6(3) 2_656 2_656 ?
O3 Eu1 O5 118.1(3) . 2_656 ?
O2 Eu1 O5 122.7(3) . 2_656 ?
O9 Eu1 C15 160.3(4) . 1_656 ?
O8 Eu1 C15 99.3(4) . 1_656 ?
O5 Eu1 C15 81.1(3) 1_556 1_656 ?
O6 Eu1 C15 27.0(4) 1_656 1_656 ?
O7 Eu1 C15 26.5(4) 1_656 1_656 ?
O4 Eu1 C15 107.0(4) 2_656 1_656 ?
O3 Eu1 C15 122.1(4) . 1_656 ?
O2 Eu1 C15 71.5(3) . 1_656 ?
O5 Eu1 C15 102.0(4) 2_656 1_656 ?
O9 Eu1 C13 101.4(4) . . ?
O8 Eu1 C13 90.2(4) . . ?
O5 Eu1 C13 171.4(4) 1_556 . ?
O6 Eu1 C13 102.6(4) 1_656 . ?
O7 Eu1 C13 93.4(4) 1_656 . ?
O4 Eu1 C13 71.7(4) 2_656 . ?
O3 Eu1 C13 26.0(4) . . ?
O2 Eu1 C13 26.5(4) . . ?
O5 Eu1 C13 122.2(3) 2_656 . ?
C15 Eu1 C13 97.6(4) 1_656 . ?
O9 Eu1 C14 76.1(4) . 2_656 ?
O8 Eu1 C14 151.4(3) . 2_656 ?
O5 Eu1 C14 91.3(3) 1_556 2_656 ?
O6 Eu1 C14 80.0(3) 1_656 2_656 ?
O7 Eu1 C14 133.5(3) 1_656 2_656 ?
O4 Eu1 C14 25.6(3) 2_656 2_656 ?
O3 Eu1 C14 96.3(4) . 2_656 ?
O2 Eu1 C14 100.2(4) . 2_656 ?
O5 Eu1 C14 25.0(3) 2_656 2_656 ?
C15 Eu1 C14 107.0(4) 1_656 2_656 ?
C13 Eu1 C14 97.2(4) . 2_656 ?
O9 Eu1 H9A 16.7 . . ?
O8 Eu1 H9A 76.8 . . ?
O5 Eu1 H9A 62.9 1_556 . ?
O6 Eu1 H9A 134.3 1_656 . ?
O7 Eu1 H9A 136.1 1_656 . ?
O4 Eu1 H9A 90.1 2_656 . ?
O3 Eu1 H9A 92.6 . . ?
O2 Eu1 H9A 144.4 . . ?
O5 Eu1 H9A 64.6 2_656 . ?
C15 Eu1 H9A 144.0 1_656 . ?
C13 Eu1 H9A 118.0 . . ?
C14 Eu1 H9A 75.4 2_656 . ?
O9 Eu1 H9B 16.7 . . ?
O8 Eu1 H9B 60.6 . . ?
O5 Eu1 H9B 85.6 1_556 . ?
O6 Eu1 H9B 163.0 1_656 . ?
O7 Eu1 H9B 133.3 1_656 . ?
O4 Eu1 H9B 95.1 2_656 . ?
O3 Eu1 H9B 66.9 . . ?
O2 Eu1 H9B 118.9 . . ?
O5 Eu1 H9B 89.0 2_656 . ?
C15 Eu1 H9B 157.5 1_656 . ?
C13 Eu1 H9B 92.8 . . ?
C14 Eu1 H9B 91.3 2_656 . ?
H9A Eu1 H9B 28.7 . . ?
HW1A OW1 HW1C 109.5 . . ?
C7 O1 C1 117.3(11) . . ?
C13 O2 Eu1 92.9(8) . . ?
C13 O3 Eu1 94.3(9) . . ?
C14 O4 Eu1 97.3(8) . 2_656 ?
C14 O5 Eu1 154.2(9) . 1_554 ?
C14 O5 Eu1 92.1(8) . 2_656 ?
Eu1 O5 Eu1 113.8(3) 1_554 2_656 ?
C15 O6 Eu1 92.7(8) . 1_454 ?
C15 O7 Eu1 91.9(9) . 1_454 ?
Eu1 O8 H8B 109.4 . . ?
Eu1 O8 H8C 109.0 . . ?
H8B O8 H8C 109.5 . . ?
Eu1 O9 H9A 109.4 . . ?
Eu1 O9 H9B 109.3 . . ?
H9A O9 H9B 109.5 . . ?
C6 C1 C2 121.3(13) . . ?
C6 C1 O1 118.7(12) . . ?
C2 C1 O1 119.8(13) . . ?
C1 C2 C3 118.1(13) . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 H2A 121.0 . . ?
C4 C3 C2 121.3(12) . . ?
C4 C3 C13 120.2(12) . . ?
C2 C3 C13 118.5(12) . . ?
C3 C4 C5 119.6(13) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
C6 C5 C4 119.9(13) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C1 C6 C5 119.7(13) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
O1 C7 C8 115.8(13) . . ?
O1 C7 C12 123.3(12) . . ?
C8 C7 C12 120.8(14) . . ?
C7 C8 C9 118.8(14) . . ?
C7 C8 C14 117.4(13) . . ?
C9 C8 C14 123.8(13) . . ?
C10 C9 C8 120.3(13) . . ?
C10 C9 C15 119.1(13) . . ?
C8 C9 C15 120.5(13) . . ?
C9 C10 C11 118.5(14) . . ?
C9 C10 H10A 120.8 . . ?
C11 C10 H10A 120.8 . . ?
C12 C11 C10 122.4(15) . . ?
C12 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
C11 C12 C7 119.1(14) . . ?
C11 C12 H12A 120.5 . . ?
C7 C12 H12A 120.5 . . ?
O3 C13 O2 119.8(12) . . ?
O3 C13 C3 121.3(13) . . ?
O2 C13 C3 118.8(12) . . ?
O3 C13 Eu1 59.7(7) . . ?
O2 C13 Eu1 60.6(7) . . ?
C3 C13 Eu1 175.0(10) . . ?
O5 C14 O4 119.9(13) . . ?
O5 C14 C8 120.3(12) . . ?
O4 C14 C8 119.4(12) . . ?
O5 C14 Eu1 62.9(8) . 2_656 ?
O4 C14 Eu1 57.1(7) . 2_656 ?
C8 C14 Eu1 169.3(9) . 2_656 ?
O7 C15 O6 121.6(13) . . ?
O7 C15 C9 120.2(13) . . ?
O6 C15 C9 118.2(13) . . ?
O7 C15 Eu1 61.5(7) . 1_454 ?
O6 C15 Eu1 60.3(7) . 1_454 ?
C9 C15 Eu1 174.1(9) . 1_454 ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.43
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         2.627
_refine_diff_density_min         -2.306
_refine_diff_density_rms         0.282
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1422775'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Eu O9.50'
_chemical_formula_weight         496.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   6.004(3)
_cell_length_b                   11.613(6)
_cell_length_c                   23.560(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.230(7)
_cell_angle_gamma                90.00
_cell_volume                     1633.1(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3273
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      27.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    3.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11985
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_sigmaI/netI    0.1292
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         27.02
_reflns_number_total             3273
_reflns_number_gt                1956
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0387P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1064
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

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 0.62063(8) 0.63841(4) 0.052318(19) 0.02346(15) Uani 1 1 d . . .
O1 O 0.4954(11) 0.2958(6) 0.1419(3) 0.0406(18) Uani 1 1 d . . .
O2 O 0.6179(9) 0.4234(5) 0.0308(2) 0.0257(14) Uani 1 1 d . . .
O3 O 0.8371(10) 0.4828(5) 0.1052(3) 0.0307(16) Uani 1 1 d . . .
O4 O 0.7210(11) 0.7923(6) -0.0113(3) 0.0354(17) Uani 1 1 d . . .
O5 O 0.8871(10) 0.6260(5) -0.0200(3) 0.0320(15) Uani 1 1 d . . .
O6 O 0.6802(10) 0.7043(6) 0.1509(3) 0.0379(18) Uani 1 1 d . . .
O7 O 0.9674(10) 0.7288(6) 0.1018(3) 0.0321(16) Uani 1 1 d . . .
O8 O 0.3047(10) 0.5540(5) 0.0921(3) 0.0341(17) Uani 1 1 d . . .
H8A H 0.2043 0.6051 0.0939 0.051 Uiso 1 1 d R . .
H8C H 0.3469 0.5289 0.1254 0.051 Uiso 1 1 d R . .
O9 O 0.3468(10) 0.7921(5) 0.0542(3) 0.0381(17) Uani 1 1 d . . .
H9A H 0.4003 0.8537 0.0416 0.057 Uiso 1 1 d R . .
H9B H 0.2283 0.7736 0.0331 0.057 Uiso 1 1 d R . .
OW1 O 0.5000 1.0000 0.0000 0.112(6) Uani 1 2 d S . .
HW1A H 0.3952 1.0277 0.0174 0.168 Uiso 0.50 1 d PR . .
HW1C H 0.4627 1.0030 -0.0358 0.168 Uiso 0.50 1 d PR . .
C1 C 0.6707(16) 0.2291(9) 0.1277(4) 0.032(2) Uani 1 1 d . . .
C2 C 0.8096(15) 0.2800(8) 0.0913(4) 0.028(2) Uani 1 1 d . . .
C3 C 0.9841(16) 0.2150(9) 0.0726(4) 0.030(2) Uani 1 1 d . . .
C4 C 1.0117(19) 0.1033(9) 0.0904(5) 0.050(3) Uani 1 1 d . . .
H4A H 1.1289 0.0605 0.0784 0.060 Uiso 1 1 calc R . .
C5 C 0.8717(19) 0.0525(9) 0.1253(5) 0.053(3) Uani 1 1 d . . .
H5A H 0.8928 -0.0239 0.1364 0.063 Uiso 1 1 calc R . .
C6 C 0.6981(19) 0.1165(9) 0.1437(5) 0.052(3) Uani 1 1 d . . .
H6A H 0.6006 0.0828 0.1669 0.062 Uiso 1 1 calc R . .
C7 C 0.7582(14) 0.4019(9) 0.0735(4) 0.027(2) Uani 1 1 d . . .
C8 C 0.8595(17) 0.7329(9) -0.0328(4) 0.034(3) Uani 1 1 d . . .
C9 C 0.4306(16) 0.3002(9) 0.1970(4) 0.032(2) Uani 1 1 d . . .
C10 C 0.5609(16) 0.2631(8) 0.2452(4) 0.035(3) Uani 1 1 d . . .
H10A H 0.7018 0.2317 0.2424 0.042 Uiso 1 1 calc R . .
C11 C 0.4798(15) 0.2733(8) 0.2985(4) 0.030(2) Uani 1 1 d . . .
C12 C 0.2695(17) 0.3216(9) 0.3008(4) 0.043(3) Uani 1 1 d . . .
H12A H 0.2093 0.3251 0.3355 0.051 Uiso 1 1 calc R . .
C13 C 0.1495(17) 0.3642(10) 0.2525(4) 0.048(3) Uani 1 1 d . . .
H13A H 0.0130 0.4005 0.2553 0.057 Uiso 1 1 calc R . .
C14 C 0.2272(15) 0.3540(10) 0.2010(4) 0.040(3) Uani 1 1 d . . .
H14A H 0.1446 0.3831 0.1685 0.048 Uiso 1 1 calc R . .
C15 C 0.8799(17) 0.7336(8) 0.1494(4) 0.033(2) 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 2.406(5) 3_665 ?
Eu1 O8 2.413(6) . ?
Eu1 O9 2.430(6) . ?
Eu1 O6 2.436(6) . ?
Eu1 O4 2.450(6) . ?
Eu1 O5 2.464(6) . ?
Eu1 O3 2.481(6) . ?
Eu1 O7 2.504(6) . ?
Eu1 O2 2.548(6) . ?
Eu1 C8 2.811(10) . ?
Eu1 C15 2.847(10) . ?
Eu1 C7 2.896(10) . ?
Eu1 H8A 2.8095 . ?
Eu1 H8C 2.8095 . ?
O1 C1 1.378(11) . ?
O1 C9 1.396(10) . ?
O2 C7 1.266(10) . ?
O2 Eu1 2.406(5) 3_665 ?
O3 C7 1.260(10) . ?
O4 C8 1.230(11) . ?
O5 C8 1.284(11) . ?
O6 C15 1.251(11) . ?
O7 C15 1.291(11) . ?
O8 H8A 0.8500 . ?
O8 H8C 0.8501 . ?
O9 H9A 0.8500 . ?
O9 H9B 0.8500 . ?
OW1 HW1A 0.8500 . ?
OW1 HW1C 0.8500 . ?
C1 C6 1.365(13) . ?
C1 C2 1.392(12) . ?
C2 C3 1.400(12) . ?
C2 C7 1.498(13) . ?
C3 C4 1.367(13) . ?
C3 C8 1.524(13) 3_765 ?
C4 C5 1.372(14) . ?
C4 H4A 0.9300 . ?
C5 C6 1.388(14) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C8 C3 1.524(13) 3_765 ?
C9 C10 1.376(12) . ?
C9 C14 1.384(12) . ?
C10 C11 1.399(12) . ?
C10 H10A 0.9300 . ?
C11 C12 1.388(13) . ?
C11 C15 1.485(12) 2_645 ?
C12 C13 1.370(13) . ?
C12 H12A 0.9300 . ?
C13 C14 1.352(12) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 C11 1.485(12) 2_655 ?

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 O8 76.8(2) 3_665 . ?
O2 Eu1 O9 83.7(2) 3_665 . ?
O8 Eu1 O9 74.3(2) . . ?
O2 Eu1 O6 152.0(2) 3_665 . ?
O8 Eu1 O6 78.3(2) . . ?
O9 Eu1 O6 77.4(2) . . ?
O2 Eu1 O4 83.3(2) 3_665 . ?
O8 Eu1 O4 142.2(2) . . ?
O9 Eu1 O4 71.8(2) . . ?
O6 Eu1 O4 109.5(2) . . ?
O2 Eu1 O5 78.1(2) 3_665 . ?
O8 Eu1 O5 147.3(2) . . ?
O9 Eu1 O5 123.1(2) . . ?
O6 Eu1 O5 129.7(2) . . ?
O4 Eu1 O5 53.0(2) . . ?
O2 Eu1 O3 115.1(2) 3_665 . ?
O8 Eu1 O3 84.3(2) . . ?
O9 Eu1 O3 147.6(2) . . ?
O6 Eu1 O3 74.6(2) . . ?
O4 Eu1 O3 133.5(2) . . ?
O5 Eu1 O3 87.7(2) . . ?
O2 Eu1 O7 153.5(2) 3_665 . ?
O8 Eu1 O7 129.7(2) . . ?
O9 Eu1 O7 102.3(2) . . ?
O6 Eu1 O7 52.8(2) . . ?
O4 Eu1 O7 74.4(2) . . ?
O5 Eu1 O7 77.1(2) . . ?
O3 Eu1 O7 73.0(2) . . ?
O2 Eu1 O2 63.6(2) 3_665 . ?
O8 Eu1 O2 72.00(19) . . ?
O9 Eu1 O2 137.2(2) . . ?
O6 Eu1 O2 119.7(2) . . ?
O4 Eu1 O2 126.1(2) . . ?
O5 Eu1 O2 78.2(2) . . ?
O3 Eu1 O2 51.54(19) . . ?
O7 Eu1 O2 119.39(19) . . ?
O2 Eu1 C8 80.9(2) 3_665 . ?
O8 Eu1 C8 156.7(2) . . ?
O9 Eu1 C8 97.2(3) . . ?
O6 Eu1 C8 121.6(3) . . ?
O4 Eu1 C8 25.9(2) . . ?
O5 Eu1 C8 27.2(2) . . ?
O3 Eu1 C8 111.2(3) . . ?
O7 Eu1 C8 72.9(2) . . ?
O2 Eu1 C8 103.5(3) . . ?
O2 Eu1 C15 174.1(2) 3_665 . ?
O8 Eu1 C15 103.3(3) . . ?
O9 Eu1 C15 90.7(2) . . ?
O6 Eu1 C15 25.9(2) . . ?
O4 Eu1 C15 93.4(3) . . ?
O5 Eu1 C15 103.8(3) . . ?
O3 Eu1 C15 70.6(2) . . ?
O7 Eu1 C15 26.9(2) . . ?
O2 Eu1 C15 122.1(2) . . ?
C8 Eu1 C15 98.3(3) . . ?
O2 Eu1 C7 89.5(2) 3_665 . ?
O8 Eu1 C7 76.7(2) . . ?
O9 Eu1 C7 151.0(2) . . ?
O6 Eu1 C7 97.1(2) . . ?
O4 Eu1 C7 135.5(2) . . ?
O5 Eu1 C7 82.5(2) . . ?
O3 Eu1 C7 25.6(2) . . ?
O7 Eu1 C7 96.3(2) . . ?
O2 Eu1 C7 25.9(2) . . ?
C8 Eu1 C7 109.6(3) . . ?
C15 Eu1 C7 96.2(3) . . ?
O2 Eu1 H8A 76.7 3_665 . ?
O8 Eu1 H8A 16.6 . . ?
O9 Eu1 H8A 57.7 . . ?
O6 Eu1 H8A 75.8 . . ?
O4 Eu1 H8A 127.0 . . ?
O5 Eu1 H8A 154.5 . . ?
O3 Eu1 H8A 99.3 . . ?
O7 Eu1 H8A 128.4 . . ?
O2 Eu1 H8A 87.0 . . ?
C8 Eu1 H8A 147.7 . . ?
C15 Eu1 H8A 101.7 . . ?
C7 Eu1 H8A 93.3 . . ?
O2 Eu1 H8C 91.6 3_665 . ?
O8 Eu1 H8C 16.6 . . ?
O9 Eu1 H8C 83.1 . . ?
O6 Eu1 H8C 66.0 . . ?
O4 Eu1 H8C 154.7 . . ?
O5 Eu1 H8C 149.7 . . ?
O3 Eu1 H8C 70.9 . . ?
O7 Eu1 H8C 114.6 . . ?
O2 Eu1 H8C 71.8 . . ?
C8 Eu1 H8C 172.3 . . ?
C15 Eu1 H8C 89.3 . . ?
C7 Eu1 H8C 68.9 . . ?
H8A Eu1 H8C 28.6 . . ?
C1 O1 C9 123.0(7) . . ?
C7 O2 Eu1 151.0(6) . 3_665 ?
C7 O2 Eu1 92.6(6) . . ?
Eu1 O2 Eu1 116.4(2) 3_665 . ?
C7 O3 Eu1 95.9(5) . . ?
C8 O4 Eu1 93.7(6) . . ?
C8 O5 Eu1 91.7(5) . . ?
C15 O6 Eu1 95.8(6) . . ?
C15 O7 Eu1 91.5(5) . . ?
Eu1 O8 H8A 109.2 . . ?
Eu1 O8 H8C 109.2 . . ?
H8A O8 H8C 109.5 . . ?
Eu1 O9 H9A 109.3 . . ?
Eu1 O9 H9B 109.2 . . ?
H9A O9 H9B 109.5 . . ?
HW1A OW1 HW1C 109.5 . . ?
C6 C1 O1 123.0(9) . . ?
C6 C1 C2 121.0(9) . . ?
O1 C1 C2 115.8(9) . . ?
C1 C2 C3 118.9(9) . . ?
C1 C2 C7 117.0(8) . . ?
C3 C2 C7 124.1(8) . . ?
C4 C3 C2 119.1(9) . . ?
C4 C3 C8 120.2(9) . 3_765 ?
C2 C3 C8 120.8(9) . 3_765 ?
C3 C4 C5 122.0(10) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C4 C5 C6 119.1(10) . . ?
C4 C5 H5A 120.4 . . ?
C6 C5 H5A 120.4 . . ?
C1 C6 C5 119.9(10) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
O3 C7 O2 119.9(9) . . ?
O3 C7 C2 119.1(8) . . ?
O2 C7 C2 120.5(8) . . ?
O3 C7 Eu1 58.4(5) . . ?
O2 C7 Eu1 61.5(5) . . ?
C2 C7 Eu1 172.0(6) . . ?
O4 C8 O5 121.4(9) . . ?
O4 C8 C3 121.3(9) . 3_765 ?
O5 C8 C3 117.2(9) . 3_765 ?
O4 C8 Eu1 60.4(5) . . ?
O5 C8 Eu1 61.2(5) . . ?
C3 C8 Eu1 172.2(7) 3_765 . ?
C10 C9 C14 120.8(9) . . ?
C10 C9 O1 124.4(9) . . ?
C14 C9 O1 114.6(8) . . ?
C9 C10 C11 119.4(9) . . ?
C9 C10 H10A 120.3 . . ?
C11 C10 H10A 120.3 . . ?
C12 C11 C10 118.4(9) . . ?
C12 C11 C15 122.0(9) . 2_645 ?
C10 C11 C15 119.6(9) . 2_645 ?
C13 C12 C11 120.8(10) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C14 C13 C12 120.8(10) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C9 119.6(9) . . ?
C13 C14 H14A 120.2 . . ?
C9 C14 H14A 120.2 . . ?
O6 C15 O7 119.7(9) . . ?
O6 C15 C11 121.4(9) . 2_655 ?
O7 C15 C11 119.0(9) . 2_655 ?
O6 C15 Eu1 58.3(5) . . ?
O7 C15 Eu1 61.5(5) . . ?
C11 C15 Eu1 175.2(7) 2_655 . ?

_diffrn_measured_fraction_theta_max 0.914
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.976
_refine_diff_density_min         -1.219
_refine_diff_density_rms         0.211
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1422776'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Gd N0 O10'
_chemical_formula_weight         510.50

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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   5.9953(8)
_cell_length_b                   11.9355(16)
_cell_length_c                   23.368(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.076(5)
_cell_angle_gamma                90.00
_cell_volume                     1659.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2977
_cell_measurement_theta_min      1.76
_cell_measurement_theta_max      25.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             988
_exptl_absorpt_coefficient_mu    4.051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8919
_diffrn_reflns_av_R_equivalents  0.1715
_diffrn_reflns_av_sigmaI/netI    0.1814
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.36
_reflns_number_total             2977
_reflns_number_gt                1740
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.1000P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     235
_refine_ls_number_restraints     60
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0734
_refine_ls_wR_factor_ref         0.2173
_refine_ls_wR_factor_gt          0.1638
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_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 0.61423(16) 0.14572(8) 0.04399(4) 0.0095(3) Uani 1 1 d . . .
O1 O 0.508(2) -0.1651(13) 0.1548(5) 0.020(3) Uani 1 1 d . . .
O2 O 0.621(2) -0.0673(10) 0.0355(5) 0.011(3) Uani 1 1 d U . .
O3 O 0.845(2) 0.0070(11) 0.1068(6) 0.017(3) Uani 1 1 d . . .
O4 O 0.705(2) 0.2798(12) -0.0293(6) 0.017(3) Uani 1 1 d U . .
O5 O 0.877(2) 0.1169(10) -0.0280(5) 0.011(3) Uani 1 1 d . . .
O6 O 0.961(2) 0.2443(11) 0.0881(6) 0.012(3) Uani 1 1 d . . .
O7 O 0.673(2) 0.2328(13) 0.1386(6) 0.023(3) Uani 1 1 d . . .
O8 O 0.307(2) 0.0703(12) 0.0897(5) 0.016(3) Uani 1 1 d . . .
H8A H 0.2029 0.1188 0.0886 0.024 Uiso 1 1 d R . .
H8C H 0.3534 0.0544 0.1246 0.024 Uiso 1 1 d R . .
O9 O 0.332(2) 0.2920(13) 0.0359(6) 0.021(3) Uani 1 1 d . . .
H9B H 0.2124 0.2679 0.0163 0.031 Uiso 1 1 d R . .
H9C H 0.3034 0.3104 0.0694 0.031 Uiso 1 1 d R . .
OW1 O 0.237(3) 0.4993(15) -0.0073(9) 0.056(6) Uani 1 1 d . . .
HW1A H 0.3297 0.5444 -0.0198 0.085 Uiso 1 1 d R . .
HW1B H 0.1278 0.4879 -0.0335 0.085 Uiso 1 1 d R . .
C1 C 0.684(3) -0.2356(17) 0.1439(8) 0.012(4) Uani 1 1 d . . .
C2 C 0.824(3) -0.1903(16) 0.1052(8) 0.010(4) Uani 1 1 d U . .
C3 C 0.999(3) -0.2584(15) 0.0908(8) 0.009(4) Uani 1 1 d U . .
C4 C 1.044(4) -0.361(2) 0.1152(10) 0.027(5) Uani 1 1 d . . .
H4A H 1.1726 -0.4021 0.1080 0.033 Uiso 1 1 calc R . .
C5 C 0.896(4) -0.4031(19) 0.1509(10) 0.028(5) Uani 1 1 d . . .
H5A H 0.9206 -0.4760 0.1668 0.033 Uiso 1 1 calc R . .
C6 C 0.716(3) -0.342(2) 0.1639(8) 0.022(5) Uani 1 1 d U . .
H6A H 0.6122 -0.3745 0.1869 0.026 Uiso 1 1 calc R . .
C7 C 0.762(3) -0.0784(15) 0.0805(7) 0.004(3) Uani 1 1 d U . .
C8 C 0.848(3) 0.2155(17) -0.0482(9) 0.017(4) Uani 1 1 d U . .
C9 C 0.442(3) -0.1628(17) 0.2095(8) 0.015(4) Uani 1 1 d U . .
C10 C 0.574(3) -0.2037(16) 0.2598(7) 0.012(4) Uani 1 1 d . . .
H10A H 0.7188 -0.2353 0.2583 0.014 Uiso 1 1 calc R . .
C11 C 0.481(3) -0.1952(17) 0.3115(8) 0.016(4) Uani 1 1 d U . .
C12 C 0.272(3) -0.150(2) 0.3142(8) 0.017(4) Uani 1 1 d . . .
H12A H 0.2085 -0.1485 0.3494 0.020 Uiso 1 1 calc R . .
C13 C 0.155(4) -0.1064(18) 0.2631(9) 0.021(5) Uani 1 1 d U . .
H13A H 0.0139 -0.0711 0.2650 0.026 Uiso 1 1 calc R . .
C14 C 0.235(3) -0.1124(17) 0.2120(9) 0.019(5) Uani 1 1 d . . .
H14A H 0.1510 -0.0829 0.1782 0.023 Uiso 1 1 calc R . .
C15 C 0.885(3) 0.2591(17) 0.1376(9) 0.017(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 O2 2.380(12) 3_655 ?
Gd1 O8 2.413(13) . ?
Gd1 O9 2.424(14) . ?
Gd1 O7 2.429(14) . ?
Gd1 O4 2.454(14) . ?
Gd1 O5 2.465(12) . ?
Gd1 O6 2.498(13) . ?
Gd1 O3 2.513(14) . ?
Gd1 O2 2.551(13) . ?
Gd1 C8 2.84(2) . ?
Gd1 C15 2.89(2) . ?
Gd1 C7 2.913(17) . ?
O1 C9 1.38(2) . ?
O1 C1 1.40(2) . ?
O2 C7 1.28(2) . ?
O2 Gd1 2.380(12) 3_655 ?
O3 C7 1.26(2) . ?
O4 C8 1.27(2) . ?
O5 C8 1.27(2) . ?
O6 C15 1.31(2) . ?
O7 C15 1.31(2) . ?
O8 H8A 0.8500 . ?
O8 H8C 0.8498 . ?
O9 H9B 0.8500 . ?
O9 H9C 0.8501 . ?
OW1 HW1A 0.8500 . ?
OW1 HW1B 0.8500 . ?
C1 C6 1.36(3) . ?
C1 C2 1.41(3) . ?
C2 C3 1.40(3) . ?
C2 C7 1.48(2) . ?
C3 C4 1.36(3) . ?
C3 C8 1.52(3) 3_755 ?
C4 C5 1.38(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.37(3) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9500 . ?
C8 C3 1.52(3) 3_755 ?
C9 C14 1.39(3) . ?
C9 C10 1.42(2) . ?
C10 C11 1.40(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.37(3) . ?
C11 C15 1.46(3) 2_645 ?
C12 C13 1.41(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.34(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 C11 1.46(3) 2_655 ?

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 O8 77.8(4) 3_655 . ?
O2 Gd1 O9 83.2(5) 3_655 . ?
O8 Gd1 O9 74.9(5) . . ?
O2 Gd1 O7 152.2(4) 3_655 . ?
O8 Gd1 O7 77.9(5) . . ?
O9 Gd1 O7 77.6(5) . . ?
O2 Gd1 O4 82.7(4) 3_655 . ?
O8 Gd1 O4 143.1(4) . . ?
O9 Gd1 O4 71.9(5) . . ?
O7 Gd1 O4 109.6(5) . . ?
O2 Gd1 O5 77.2(4) 3_655 . ?
O8 Gd1 O5 146.7(5) . . ?
O9 Gd1 O5 123.1(4) . . ?
O7 Gd1 O5 130.3(4) . . ?
O4 Gd1 O5 53.0(4) . . ?
O2 Gd1 O6 152.8(4) 3_655 . ?
O8 Gd1 O6 129.4(4) . . ?
O9 Gd1 O6 103.4(5) . . ?
O7 Gd1 O6 53.3(4) . . ?
O4 Gd1 O6 74.6(4) . . ?
O5 Gd1 O6 77.2(4) . . ?
O2 Gd1 O3 115.3(4) 3_655 . ?
O8 Gd1 O3 83.8(4) . . ?
O9 Gd1 O3 148.2(4) . . ?
O7 Gd1 O3 75.1(5) . . ?
O4 Gd1 O3 133.1(4) . . ?
O5 Gd1 O3 87.4(4) . . ?
O6 Gd1 O3 72.5(4) . . ?
O2 Gd1 O2 63.9(5) 3_655 . ?
O8 Gd1 O2 71.5(4) . . ?
O9 Gd1 O2 136.8(4) . . ?
O7 Gd1 O2 119.7(5) . . ?
O4 Gd1 O2 126.1(4) . . ?
O5 Gd1 O2 77.9(4) . . ?
O6 Gd1 O2 118.8(4) . . ?
O3 Gd1 O2 51.4(4) . . ?
O2 Gd1 C8 79.8(5) 3_655 . ?
O8 Gd1 C8 157.1(5) . . ?
O9 Gd1 C8 97.8(5) . . ?
O7 Gd1 C8 122.3(5) . . ?
O4 Gd1 C8 26.5(5) . . ?
O5 Gd1 C8 26.6(5) . . ?
O6 Gd1 C8 73.2(5) . . ?
O3 Gd1 C8 110.4(5) . . ?
O2 Gd1 C8 102.7(5) . . ?
O2 Gd1 C15 175.2(5) 3_655 . ?
O8 Gd1 C15 103.1(5) . . ?
O9 Gd1 C15 92.5(5) . . ?
O7 Gd1 C15 26.6(5) . . ?
O4 Gd1 C15 94.1(5) . . ?
O5 Gd1 C15 103.7(5) . . ?
O6 Gd1 C15 26.8(5) . . ?
O3 Gd1 C15 69.5(5) . . ?
O2 Gd1 C15 120.8(5) . . ?
C8 Gd1 C15 98.8(6) . . ?
O2 Gd1 C7 89.8(4) 3_655 . ?
O8 Gd1 C7 75.5(5) . . ?
O9 Gd1 C7 150.4(5) . . ?
O7 Gd1 C7 96.9(5) . . ?
O4 Gd1 C7 135.8(5) . . ?
O5 Gd1 C7 82.8(4) . . ?
O6 Gd1 C7 96.0(4) . . ?
O3 Gd1 C7 25.5(4) . . ?
O2 Gd1 C7 25.9(4) . . ?
C8 Gd1 C7 109.3(5) . . ?
C15 Gd1 C7 94.9(5) . . ?
C9 O1 C1 119.2(14) . . ?
C7 O2 Gd1 150.8(11) . 3_655 ?
C7 O2 Gd1 93.1(10) . . ?
Gd1 O2 Gd1 116.1(5) 3_655 . ?
C7 O3 Gd1 95.3(10) . . ?
C8 O4 Gd1 93.9(12) . . ?
C8 O5 Gd1 93.3(12) . . ?
C15 O6 Gd1 93.7(11) . . ?
C15 O7 Gd1 96.9(12) . . ?
Gd1 O8 H8A 109.3 . . ?
Gd1 O8 H8C 109.4 . . ?
H8A O8 H8C 109.5 . . ?
Gd1 O9 H9B 109.4 . . ?
Gd1 O9 H9C 109.3 . . ?
H9B O9 H9C 109.5 . . ?
HW1A OW1 HW1B 109.5 . . ?
C6 C1 O1 125.1(18) . . ?
C6 C1 C2 120.8(18) . . ?
O1 C1 C2 114.0(16) . . ?
C3 C2 C1 116.7(17) . . ?
C3 C2 C7 126.0(17) . . ?
C1 C2 C7 117.1(16) . . ?
C4 C3 C2 122.5(18) . . ?
C4 C3 C8 118.1(17) . 3_755 ?
C2 C3 C8 119.4(16) . 3_755 ?
C5 C4 C3 118(2) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
C4 C5 C6 122(2) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C1 C6 C5 120(2) . . ?
C1 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
O3 C7 O2 120.1(16) . . ?
O3 C7 C2 118.3(14) . . ?
O2 C7 C2 121.5(15) . . ?
O3 C7 Gd1 59.2(9) . . ?
O2 C7 Gd1 61.0(9) . . ?
C2 C7 Gd1 173.3(12) . . ?
O4 C8 O5 119.6(19) . . ?
O4 C8 C3 120.7(17) . 3_755 ?
O5 C8 C3 119.4(17) . 3_755 ?
O4 C8 Gd1 59.6(10) . . ?
O5 C8 Gd1 60.1(10) . . ?
C3 C8 Gd1 171.5(13) 3_755 . ?
C14 C9 O1 113.9(16) . . ?
C14 C9 C10 121.7(18) . . ?
O1 C9 C10 124.4(17) . . ?
C11 C10 C9 116.7(18) . . ?
C11 C10 H10A 121.6 . . ?
C9 C10 H10A 121.6 . . ?
C12 C11 C10 122.2(18) . . ?
C12 C11 C15 121.8(18) . 2_645 ?
C10 C11 C15 116.0(18) . 2_645 ?
C11 C12 C13 118.1(18) . . ?
C11 C12 H12A 121.0 . . ?
C13 C12 H12A 121.0 . . ?
C14 C13 C12 123(2) . . ?
C14 C13 H13A 118.7 . . ?
C12 C13 H13A 118.7 . . ?
C13 C14 C9 118.6(19) . . ?
C13 C14 H14A 120.7 . . ?
C9 C14 H14A 120.7 . . ?
O7 C15 O6 115.3(17) . . ?
O7 C15 C11 121.1(18) . 2_655 ?
O6 C15 C11 123.6(18) . 2_655 ?
O7 C15 Gd1 56.4(10) . . ?
O6 C15 Gd1 59.5(10) . . ?
C11 C15 Gd1 173.6(15) 2_655 . ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.36
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         1.745
_refine_diff_density_min         -2.631
_refine_diff_density_rms         0.635
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1422777'
_audit_update_record             
;
2015-09-07 deposited with the CCDC.
2016-05-03 downloaded from the CCDC.
;

#================================================================ 

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 O9.50 Tb'
_chemical_formula_weight         503.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   5.974(8)
_cell_length_b                   11.590(16)
_cell_length_c                   23.47(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.391(17)
_cell_angle_gamma                90.00
_cell_volume                     1615(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3237
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      27.13

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.069
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             972
_exptl_absorpt_coefficient_mu    4.431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7371
_exptl_absorpt_correction_T_max  0.7846
_exptl_absorpt_process_details   ?

_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 Smart APEX CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11696
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_av_sigmaI/netI    0.0957
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         27.13
_reflns_number_total             3237
_reflns_number_gt                2355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 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)+(0.0546P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.002

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
Tb1 Tb 0.12020(5) 0.63774(3) 0.052141(16) 0.02155(15) Uani 1 1 d . . .
O1 O 1.0028(9) 0.7037(5) -0.1420(2) 0.0354(14) Uani 1 1 d . . .
O2 O 0.4641(8) 0.7285(5) 0.1010(2) 0.0319(13) Uani 1 1 d . . .
O3 O 0.1782(8) 0.7027(5) 0.1504(2) 0.0342(14) Uani 1 1 d . . .
O4 O 0.1170(7) 0.4232(4) 0.0304(2) 0.0235(11) Uani 1 1 d . . .
O5 O 0.3398(8) 0.4848(4) 0.1045(2) 0.0289(13) Uani 1 1 d . . .
O6 O 0.2177(9) 0.7914(5) -0.0115(2) 0.0355(14) Uani 1 1 d . . .
O7 O 0.3856(8) 0.6248(4) -0.0192(3) 0.0299(14) Uani 1 1 d . . .
O8 O -0.1923(8) 0.5536(4) 0.0908(2) 0.0327(13) Uani 1 1 d . . .
H8A H -0.2946 0.6041 0.0923 0.049 Uiso 1 1 d R . .
H8C H -0.1503 0.5289 0.1244 0.049 Uiso 1 1 d R . .
O9 O -0.1503(9) 0.7918(5) 0.0539(2) 0.0374(14) Uani 1 1 d . . .
H9A H -0.0970 0.8530 0.0407 0.056 Uiso 1 1 d R . .
H9B H -0.2703 0.7728 0.0331 0.056 Uiso 1 1 d R . .
OW1 O 0.0000 1.0000 0.0000 0.111(5) Uani 1 2 d S . .
HW1A H -0.1114 1.0263 0.0155 0.167 Uiso 0.50 1 d PR . .
HW1C H -0.0284 1.0036 -0.0363 0.167 Uiso 0.50 1 d PR . .
C1 C 0.5642(12) 0.8014(7) 0.3032(3) 0.0283(18) Uani 1 1 d . . .
C2 C 0.4351(12) 0.7619(6) 0.2543(3) 0.0268(18) Uani 1 1 d . . .
H2A H 0.2947 0.7288 0.2570 0.032 Uiso 1 1 calc R . .
C3 C 0.5174(12) 0.7720(7) 0.2012(3) 0.0283(18) Uani 1 1 d . . .
C4 C 0.7286(13) 0.8219(7) 0.1980(4) 0.034(2) Uani 1 1 d . . .
H4A H 0.7873 0.8266 0.1630 0.041 Uiso 1 1 calc R . .
C5 C 0.8495(13) 0.8642(7) 0.2472(4) 0.040(2) Uani 1 1 d . . .
H5A H 0.9878 0.8996 0.2449 0.048 Uiso 1 1 calc R . .
C6 C 0.7681(13) 0.8546(7) 0.2996(4) 0.035(2) Uani 1 1 d . . .
H6A H 0.8504 0.8839 0.3324 0.041 Uiso 1 1 calc R . .
C7 C 0.8261(12) 0.7712(7) -0.1279(3) 0.0272(18) Uani 1 1 d . . .
C8 C 0.6885(12) 0.7196(6) -0.0914(3) 0.0250(18) Uani 1 1 d . . .
C9 C 0.5124(12) 0.7830(6) -0.0724(3) 0.0250(18) Uani 1 1 d . . .
C10 C 0.4795(16) 0.8964(8) -0.0895(4) 0.046(3) Uani 1 1 d . . .
H10A H 0.3629 0.9390 -0.0767 0.055 Uiso 1 1 calc R . .
C11 C 0.6199(16) 0.9469(8) -0.1256(4) 0.053(3) Uani 1 1 d . . .
H11A H 0.5966 1.0231 -0.1373 0.064 Uiso 1 1 calc R . .
C12 C 0.7949(15) 0.8841(7) -0.1445(4) 0.043(2) Uani 1 1 d . . .
H12A H 0.8905 0.9183 -0.1682 0.052 Uiso 1 1 calc R . .
C13 C 0.3807(12) 0.7321(6) 0.1489(4) 0.0269(18) Uani 1 1 d . . .
C14 C 0.2592(11) 0.4038(7) 0.0742(4) 0.0258(18) Uani 1 1 d . . .
C15 C 0.3645(12) 0.7298(7) -0.0322(3) 0.0260(18) 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
Tb1 O8 2.375(5) . ?
Tb1 O4 2.376(5) 3_565 ?
Tb1 O9 2.412(6) . ?
Tb1 O3 2.415(6) . ?
Tb1 O7 2.436(5) . ?
Tb1 O6 2.437(6) . ?
Tb1 O5 2.452(5) . ?
Tb1 O2 2.473(6) . ?
Tb1 O4 2.538(6) . ?
Tb1 C15 2.799(8) . ?
Tb1 C13 2.826(9) . ?
Tb1 C14 2.866(9) . ?
O1 C1 1.379(9) 4_675 ?
O1 C7 1.383(8) . ?
O2 C13 1.281(9) . ?
O3 C13 1.261(8) . ?
O4 C14 1.278(9) . ?
O4 Tb1 2.376(5) 3_565 ?
O5 C14 1.243(9) . ?
O6 C15 1.270(8) . ?
O7 C15 1.257(8) . ?
O8 H8A 0.8500 . ?
O8 H8C 0.8499 . ?
O9 H9A 0.8500 . ?
O9 H9B 0.8499 . ?
OW1 HW1A 0.8500 . ?
OW1 HW1C 0.8501 . ?
C1 O1 1.379(9) 4_576 ?
C1 C6 1.376(11) . ?
C1 C2 1.386(10) . ?
C2 C3 1.395(11) . ?
C2 H2A 0.9300 . ?
C3 C4 1.398(10) . ?
C3 C13 1.472(11) . ?
C4 C5 1.382(12) . ?
C4 H4A 0.9300 . ?
C5 C6 1.377(12) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C12 1.373(10) . ?
C7 C8 1.387(10) . ?
C8 C9 1.396(10) . ?
C8 C14 1.509(11) 3_665 ?
C9 C10 1.383(11) . ?
C9 C15 1.495(10) . ?
C10 C11 1.387(12) . ?
C10 H10A 0.9300 . ?
C11 C12 1.385(12) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C14 C8 1.509(11) 3_665 ?

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
O8 Tb1 O4 76.5(2) . 3_565 ?
O8 Tb1 O9 75.0(2) . . ?
O4 Tb1 O9 83.91(19) 3_565 . ?
O8 Tb1 O3 78.35(19) . . ?
O4 Tb1 O3 151.69(16) 3_565 . ?
O9 Tb1 O3 77.17(19) . . ?
O8 Tb1 O7 146.85(18) . . ?
O4 Tb1 O7 78.2(2) 3_565 . ?
O9 Tb1 O7 123.09(18) . . ?
O3 Tb1 O7 129.87(19) . . ?
O8 Tb1 O6 141.86(18) . . ?
O4 Tb1 O6 83.1(2) 3_565 . ?
O9 Tb1 O6 71.07(19) . . ?
O3 Tb1 O6 109.8(2) . . ?
O7 Tb1 O6 53.49(17) . . ?
O8 Tb1 O5 84.89(19) . . ?
O4 Tb1 O5 115.53(18) 3_565 . ?
O9 Tb1 O5 148.07(19) . . ?
O3 Tb1 O5 74.6(2) . . ?
O7 Tb1 O5 86.97(19) . . ?
O6 Tb1 O5 133.19(18) . . ?
O8 Tb1 O2 130.2(2) . . ?
O4 Tb1 O2 153.30(17) 3_565 . ?
O9 Tb1 O2 101.6(2) . . ?
O3 Tb1 O2 53.22(17) . . ?
O7 Tb1 O2 76.9(2) . . ?
O6 Tb1 O2 74.4(2) . . ?
O5 Tb1 O2 72.83(19) . . ?
O8 Tb1 O4 71.70(17) . . ?
O4 Tb1 O4 63.54(19) 3_565 . ?
O9 Tb1 O4 137.63(17) . . ?
O3 Tb1 O4 119.66(18) . . ?
O7 Tb1 O4 78.00(16) . . ?
O6 Tb1 O4 126.13(18) . . ?
O5 Tb1 O4 52.01(17) . . ?
O2 Tb1 O4 119.82(17) . . ?
O8 Tb1 C15 157.1(2) . . ?
O4 Tb1 C15 81.2(2) 3_565 . ?
O9 Tb1 C15 97.6(2) . . ?
O3 Tb1 C15 121.8(2) . . ?
O7 Tb1 C15 26.65(18) . . ?
O6 Tb1 C15 26.94(18) . . ?
O5 Tb1 C15 109.7(2) . . ?
O2 Tb1 C15 72.2(2) . . ?
O4 Tb1 C15 102.9(2) . . ?
O8 Tb1 C13 103.7(2) . . ?
O4 Tb1 C13 174.22(19) 3_565 . ?
O9 Tb1 C13 90.6(2) . . ?
O3 Tb1 C13 26.38(18) . . ?
O7 Tb1 C13 103.5(2) . . ?
O6 Tb1 C13 93.6(2) . . ?
O5 Tb1 C13 70.2(2) . . ?
O2 Tb1 C13 26.93(18) . . ?
O4 Tb1 C13 122.13(19) . . ?
C15 Tb1 C13 97.9(2) . . ?
O8 Tb1 C14 76.51(19) . . ?
O4 Tb1 C14 90.0(2) 3_565 . ?
O9 Tb1 C14 151.49(18) . . ?
O3 Tb1 C14 96.6(2) . . ?
O7 Tb1 C14 82.42(18) . . ?
O6 Tb1 C14 135.88(18) . . ?
O5 Tb1 C14 25.54(19) . . ?
O2 Tb1 C14 96.3(2) . . ?
O4 Tb1 C14 26.5(2) . . ?
C15 Tb1 C14 108.9(2) . . ?
C13 Tb1 C14 95.7(2) . . ?
C1 O1 C7 122.4(6) 4_675 . ?
C13 O2 Tb1 92.1(4) . . ?
C13 O3 Tb1 95.4(5) . . ?
C14 O4 Tb1 152.3(5) . 3_565 ?
C14 O4 Tb1 91.2(5) . . ?
Tb1 O4 Tb1 116.46(19) 3_565 . ?
C14 O5 Tb1 96.2(5) . . ?
C15 O6 Tb1 92.6(5) . . ?
C15 O7 Tb1 93.0(4) . . ?
Tb1 O8 H8A 109.4 . . ?
Tb1 O8 H8C 109.2 . . ?
H8A O8 H8C 109.5 . . ?
Tb1 O9 H9A 109.4 . . ?
Tb1 O9 H9B 108.8 . . ?
H9A O9 H9B 109.5 . . ?
HW1A OW1 HW1C 109.5 . . ?
O1 C1 C6 113.9(7) 4_576 . ?
O1 C1 C2 125.2(7) 4_576 . ?
C6 C1 C2 120.9(7) . . ?
C1 C2 C3 119.4(7) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C2 C3 C4 119.6(7) . . ?
C2 C3 C13 120.1(7) . . ?
C4 C3 C13 120.3(7) . . ?
C5 C4 C3 119.5(8) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C6 C5 C4 121.0(8) . . ?
C6 C5 H5A 119.5 . . ?
C4 C5 H5A 119.5 . . ?
C5 C6 C1 119.5(8) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
C12 C7 C8 121.0(7) . . ?
C12 C7 O1 123.7(7) . . ?
C8 C7 O1 115.1(7) . . ?
C7 C8 C9 119.3(7) . . ?
C7 C8 C14 117.1(6) . 3_665 ?
C9 C8 C14 123.6(6) . 3_665 ?
C10 C9 C8 119.7(7) . . ?
C10 C9 C15 120.0(7) . . ?
C8 C9 C15 120.3(7) . . ?
C11 C10 C9 120.1(8) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.2(8) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C7 C12 C11 119.6(8) . . ?
C7 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
O3 C13 O2 119.0(7) . . ?
O3 C13 C3 120.4(7) . . ?
O2 C13 C3 120.6(7) . . ?
O3 C13 Tb1 58.3(4) . . ?
O2 C13 Tb1 61.0(4) . . ?
C3 C13 Tb1 175.5(6) . . ?
O5 C14 O4 120.5(7) . . ?
O5 C14 C8 120.5(7) . 3_665 ?
O4 C14 C8 118.8(7) . 3_665 ?
O5 C14 Tb1 58.3(4) . . ?
O4 C14 Tb1 62.3(4) . . ?
C8 C14 Tb1 172.7(5) 3_665 . ?
O7 C15 O6 120.4(7) . . ?
O7 C15 C9 120.2(6) . . ?
O6 C15 C9 119.4(7) . . ?
O7 C15 Tb1 60.3(4) . . ?
O6 C15 Tb1 60.4(4) . . ?
C9 C15 Tb1 174.1(6) . . ?

_diffrn_measured_fraction_theta_max 0.905
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.694
_refine_diff_density_min         -2.159
_refine_diff_density_rms         0.248
