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

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

data_x
_database_code_depnum_ccdc_archive 'CCDC 1450972'
_audit_update_record             
;
2016-01-31 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H8 Eu O12, C10 H19 N2'
_chemical_formula_sum            'C26 H27 Eu N2 O12'
_chemical_formula_weight         711.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   27.8885(7)
_cell_length_b                   11.4437(3)
_cell_length_c                   17.7204(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5655.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3459
_cell_measurement_theta_min      2.8190
_cell_measurement_theta_max      28.6610

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_F_000             2848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    2.284
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.97464
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.2083
_diffrn_reflns_number            17156
_diffrn_reflns_av_unetI/netI     0.0792
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6193
_reflns_number_gt                4142
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond 3'
_computing_publication_material  'office 2007'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+2.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6193
_refine_ls_number_parameters     513
_refine_ls_number_restraints     1025
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.06808(2) 0.18380(2) 0.22246(2) 0.01165(8) Uani 1 1 d . . . . .
O1 O 0.12485(13) 0.3020(3) 0.1497(2) 0.0244(9) Uani 1 1 d . . . . .
O2 O 0.13729(14) 0.3041(3) 0.2721(2) 0.0301(10) Uani 1 1 d . . . . .
O3 O 0.35122(14) 0.5346(4) 0.0853(3) 0.0426(12) Uani 1 1 d . . . . .
O4 O 0.36188(13) 0.5617(3) 0.2076(2) 0.0280(10) Uani 1 1 d . . . . .
O5 O 0.1946(9) 0.339(3) 0.0585(10) 0.038(5) Uani 0.54(7) 1 d D U P A 1
H5A H 0.1683 0.3137 0.0712 0.057 Uiso 0.54(7) 1 calc R U P A 1
O6 O 0.2896(11) 0.535(4) 0.3008(10) 0.066(7) Uani 0.54(7) 1 d D U P A 1
H6A H 0.3184 0.5446 0.2937 0.099 Uiso 0.54(7) 1 calc R U P A 1
O5B O 0.1878(12) 0.378(4) 0.0564(12) 0.055(7) Uani 0.46(7) 1 d D U P A 2
H5B H 0.1618 0.3511 0.0689 0.082 Uiso 0.46(7) 1 calc R U P A 2
O6B O 0.3002(9) 0.483(4) 0.3029(10) 0.048(7) Uani 0.46(7) 1 d D U P A 2
H6B H 0.3266 0.5059 0.2893 0.072 Uiso 0.46(7) 1 calc R U P A 2
O7 O 0.08154(12) 0.1167(3) 0.3568(2) 0.0234(9) Uani 1 1 d . . . . .
O8 O 0.01064(12) 0.1868(3) 0.32865(19) 0.0159(8) Uani 1 1 d . . . . .
O9 O -0.06504(12) 0.1151(3) 0.4085(2) 0.0203(8) Uani 1 1 d . . . . .
H9A H -0.0914 0.0842 0.4133 0.030 Uiso 1 1 calc R U . . .
O10 O 0.03799(13) -0.0141(3) 0.2300(2) 0.0255(10) Uani 1 1 d . . . . .
O11 O 0.03803(13) -0.6210(3) 0.2306(2) 0.0254(10) Uani 1 1 d . . . . .
O12A O 0.0801(3) -0.2074(7) 0.1939(6) 0.055(3) Uani 0.5 1 d . U P B 1
H12B H 0.0784 -0.1361 0.1974 0.082 Uiso 0.5 1 calc R U P B 1
O12B O 0.0791(3) -0.4304(6) 0.1927(6) 0.051(3) Uani 0.5 1 d . U P C 2
H12C H 0.0767 -0.5016 0.1967 0.076 Uiso 0.5 1 calc R U P C 2
C1 C 0.1503(2) 0.3293(5) 0.2063(3) 0.0223(13) Uani 1 1 d . . . . .
C2 C 0.1979(2) 0.3855(5) 0.1923(3) 0.0231(13) Uani 1 1 d . . . . .
C3 C 0.2164(2) 0.3927(6) 0.1200(3) 0.0329(16) Uani 1 1 d D . . . .
C4 C 0.2615(2) 0.4391(6) 0.1080(4) 0.0383(17) Uani 1 1 d . . . . .
H4A H 0.2737 0.4430 0.0592 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2887(2) 0.4798(5) 0.1679(4) 0.0296(15) Uani 1 1 d . . . . .
C6 C 0.2699(2) 0.4734(7) 0.2401(4) 0.047(2) Uani 1 1 d D . . . .
C7 C 0.2251(2) 0.4263(6) 0.2520(4) 0.0413(19) Uani 1 1 d . . . . .
H7A H 0.2129 0.4219 0.3008 0.050 Uiso 1 1 calc R U . . .
C8 C 0.3375(2) 0.5280(5) 0.1515(4) 0.0284(15) Uani 1 1 d . . . . .
C9 C 0.03764(18) 0.1251(4) 0.3718(3) 0.0162(12) Uani 1 1 d . . . . .
C10 C 0.01653(18) 0.0635(4) 0.4376(3) 0.0167(12) Uani 1 1 d . . . . .
C11 C -0.03243(18) 0.0583(4) 0.4529(3) 0.0154(11) Uani 1 1 d . . . . .
C12 C -0.04772(19) -0.0041(5) 0.5145(3) 0.0214(13) Uani 1 1 d . . . . .
H12A H -0.0804 -0.0069 0.5247 0.026 Uiso 1 1 calc R U . . .
C13 C 0.0000 -0.0641(6) 0.2500 0.0192(18) Uani 1 2 d S T P . .
C14 C 0.0000 -0.1950(6) 0.2500 0.0224(18) Uani 1 2 d S T P B .
C15 C 0.0386(2) -0.2569(5) 0.2215(4) 0.0298(15) Uani 1 1 d . . . . .
H15A H 0.0655 -0.2148 0.2014 0.036 Uiso 0.5 1 d R U P B 2
C16 C 0.0392(2) -0.3784(5) 0.2219(4) 0.0266(14) Uani 1 1 d . . . . .
H16A H 0.0664 -0.4206 0.2028 0.032 Uiso 0.5 1 d R U P C 1
C17 C 0.0000 -0.4387(6) 0.2500 0.0205(18) Uani 1 2 d S T P C .
C18 C 0.0000 -0.5695(6) 0.2500 0.0196(18) Uani 1 2 d S T P . .
N1 N 0.1962(6) 0.7165(14) -0.0293(10) 0.109(4) Uani 0.472(7) 1 d D U P D 1
N2 N 0.1298(7) 0.6886(17) 0.0083(14) 0.119(3) Uani 0.472(7) 1 d D U P D 1
C20 C 0.2031(7) 0.6882(15) 0.0445(11) 0.113(4) Uani 0.472(7) 1 d D U P D 1
H20A H 0.2318 0.6830 0.0711 0.136 Uiso 0.472(7) 1 calc R U P D 1
C21 C 0.1565(8) 0.6687(15) 0.0703(10) 0.115(4) Uani 0.472(7) 1 d D U P D 1
H21A H 0.1464 0.6474 0.1184 0.138 Uiso 0.472(7) 1 calc R U P D 1
C22 C 0.1516(8) 0.7190(16) -0.0573(10) 0.114(4) Uani 0.472(7) 1 d D U P D 1
H22A H 0.1396 0.7357 -0.1051 0.137 Uiso 0.472(7) 1 calc R U P D 1
C23 C 0.0800(8) 0.6605(16) 0.0033(15) 0.116(4) Uani 0.472(7) 1 d D U P D 1
H23A H 0.0636 0.7005 -0.0376 0.139 Uiso 0.472(7) 1 calc R U P D 1
H23B H 0.0629 0.6711 0.0505 0.139 Uiso 0.472(7) 1 calc R U P D 1
C24 C 0.0913(8) 0.5324(16) -0.0143(15) 0.123(4) Uani 0.472(7) 1 d D U P D 1
H24A H 0.0909 0.4896 0.0329 0.148 Uiso 0.472(7) 1 calc R U P D 1
H24B H 0.1239 0.5289 -0.0335 0.148 Uiso 0.472(7) 1 calc R U P D 1
C25 C 0.0586(8) 0.4671(15) -0.0706(12) 0.121(4) Uani 0.472(7) 1 d D U P D 1
H25A H 0.0666 0.4933 -0.1211 0.146 Uiso 0.472(7) 1 calc R U P D 1
H25B H 0.0257 0.4901 -0.0608 0.146 Uiso 0.472(7) 1 calc R U P D 1
C26 C 0.0612(6) 0.3321(15) -0.0692(14) 0.126(5) Uani 0.472(7) 1 d D U P D 1
H26A H 0.0498 0.3058 -0.0204 0.151 Uiso 0.472(7) 1 calc R U P D 1
H26B H 0.0391 0.3025 -0.1069 0.151 Uiso 0.472(7) 1 calc R U P D 1
C27 C 0.1106(8) 0.276(2) -0.0836(16) 0.127(5) Uani 0.472(7) 1 d D U P D 1
H27A H 0.1314 0.2964 -0.0417 0.152 Uiso 0.472(7) 1 calc R U P D 1
H27B H 0.1065 0.1916 -0.0822 0.152 Uiso 0.472(7) 1 calc R U P D 1
C28 C 0.1372(10) 0.306(3) -0.1572(16) 0.179(8) Uani 0.472(7) 1 d D U P D 1
H28A H 0.1624 0.2509 -0.1657 0.268 Uiso 0.472(7) 1 calc R U P D 1
H28B H 0.1506 0.3834 -0.1532 0.268 Uiso 0.472(7) 1 calc R U P D 1
H28C H 0.1150 0.3042 -0.1987 0.268 Uiso 0.472(7) 1 calc R U P D 1
C29 C 0.2386(8) 0.742(3) -0.0717(16) 0.112(6) Uani 0.472(7) 1 d D U P D 1
H29A H 0.2301 0.7832 -0.1169 0.168 Uiso 0.472(7) 1 calc R U P D 1
H29B H 0.2544 0.6702 -0.0848 0.168 Uiso 0.472(7) 1 calc R U P D 1
H29C H 0.2597 0.7893 -0.0419 0.168 Uiso 0.472(7) 1 calc R U P D 1
N1B N 0.2238(6) 0.7529(16) -0.0631(10) 0.114(4) Uani 0.528(7) 1 d D U P D 2
N2B N 0.1626(5) 0.7195(14) -0.0053(9) 0.110(3) Uani 0.528(7) 1 d D U P D 2
C20B C 0.2387(6) 0.6766(15) -0.0089(11) 0.111(4) Uani 0.528(7) 1 d D U P D 2
H20B H 0.2694 0.6471 -0.0005 0.134 Uiso 0.528(7) 1 calc R U P D 2
C21B C 0.1964(7) 0.6536(14) 0.0311(9) 0.112(4) Uani 0.528(7) 1 d D U P D 2
H21B H 0.1922 0.6050 0.0726 0.135 Uiso 0.528(7) 1 calc R U P D 2
C22B C 0.1770(6) 0.7841(14) -0.0648(9) 0.112(4) Uani 0.528(7) 1 d D U P D 2
H22C H 0.1602 0.8340 -0.0967 0.134 Uiso 0.528(7) 1 calc R U P D 2
C23B C 0.1133(6) 0.6935(19) 0.0128(14) 0.119(3) Uani 0.528(7) 1 d D U P D 2
H23C H 0.0991 0.7690 0.0238 0.142 Uiso 0.528(7) 1 calc R U P D 2
H23D H 0.1149 0.6528 0.0608 0.142 Uiso 0.528(7) 1 calc R U P D 2
C24B C 0.0741(7) 0.6273(14) -0.0326(12) 0.115(4) Uani 0.528(7) 1 d D U P D 2
H24C H 0.0431 0.6591 -0.0185 0.138 Uiso 0.528(7) 1 calc R U P D 2
H24D H 0.0788 0.6443 -0.0857 0.138 Uiso 0.528(7) 1 calc R U P D 2
C25B C 0.0718(7) 0.4933(13) -0.0233(11) 0.126(4) Uani 0.528(7) 1 d D U P D 2
H25C H 0.0828 0.4746 0.0272 0.151 Uiso 0.528(7) 1 calc R U P D 2
H25D H 0.0385 0.4699 -0.0265 0.151 Uiso 0.528(7) 1 calc R U P D 2
C26B C 0.1004(7) 0.4183(12) -0.0789(12) 0.131(4) Uani 0.528(7) 1 d D U P D 2
H26C H 0.1341 0.4265 -0.0664 0.157 Uiso 0.528(7) 1 calc R U P D 2
H26D H 0.0959 0.4514 -0.1288 0.157 Uiso 0.528(7) 1 calc R U P D 2
C27B C 0.0893(8) 0.2871(14) -0.0840(15) 0.131(5) Uani 0.528(7) 1 d D U P D 2
H27C H 0.0601 0.2777 -0.1129 0.157 Uiso 0.528(7) 1 calc R U P D 2
H27D H 0.0829 0.2590 -0.0333 0.157 Uiso 0.528(7) 1 calc R U P D 2
C28B C 0.1282(9) 0.2071(17) -0.1194(16) 0.181(8) Uani 0.528(7) 1 d D U P D 2
H28D H 0.1372 0.1478 -0.0839 0.271 Uiso 0.528(7) 1 calc R U P D 2
H28E H 0.1559 0.2530 -0.1322 0.271 Uiso 0.528(7) 1 calc R U P D 2
H28F H 0.1157 0.1710 -0.1642 0.271 Uiso 0.528(7) 1 calc R U P D 2
C29B C 0.2581(7) 0.801(2) -0.1153(12) 0.132(6) Uani 0.528(7) 1 d D U P D 2
H29D H 0.2426 0.8175 -0.1624 0.198 Uiso 0.528(7) 1 calc R U P D 2
H29E H 0.2834 0.7452 -0.1235 0.198 Uiso 0.528(7) 1 calc R U P D 2
H29F H 0.2713 0.8715 -0.0948 0.198 Uiso 0.528(7) 1 calc R U P D 2


_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 O8 2.375(3) 4 ?
Eu1 O11 2.390(3) 1_565 ?
Eu1 O4 2.416(3) 7_655 ?
Eu1 O10 2.419(3) . ?
Eu1 O1 2.449(3) . ?
Eu1 O9 2.452(3) 4 ?
Eu1 O8 2.472(3) . ?
Eu1 O2 2.528(4) . ?
Eu1 O7 2.529(4) . ?
Eu1 C1 2.849(5) . ?
Eu1 C9 2.858(6) . ?
Eu1 Eu1 3.9205(5) 4 ?
O1 C1 1.269(6) . ?
O2 C1 1.253(6) . ?
O3 C8 1.236(7) . ?
O4 C8 1.264(7) . ?
O4 Eu1 2.416(3) 7_665 ?
O5 C3 1.390(8) . ?
O6 C6 1.399(8) . ?
O5B C3 1.391(9) . ?
O6B C6 1.399(8) . ?
O7 C9 1.256(6) . ?
O8 C9 1.284(6) . ?
O8 Eu1 2.375(3) 4 ?
O9 C11 1.367(6) . ?
O9 Eu1 2.452(3) 4 ?
O10 C13 1.255(4) . ?
O11 C18 1.261(5) . ?
O11 Eu1 2.390(3) 1_545 ?
O12A C15 1.379(9) . ?
O12B C16 1.365(9) . ?
C1 C2 1.496(7) . ?
C2 C3 1.383(8) . ?
C2 C7 1.382(8) . ?
C3 C4 1.382(7) . ?
C4 C5 1.385(8) . ?
C5 C6 1.384(9) . ?
C5 C8 1.499(7) . ?
C6 C7 1.379(8) . ?
C9 C10 1.485(7) . ?
C10 C12 1.393(7) 5_556 ?
C10 C11 1.393(7) . ?
C11 C12 1.373(7) . ?
C12 C10 1.393(7) 5_556 ?
C13 O10 1.255(4) 4 ?
C13 C14 1.498(9) . ?
C14 C15 1.384(6) 4 ?
C14 C15 1.384(6) . ?
C15 C16 1.391(7) . ?
C16 C17 1.385(6) . ?
C17 C16 1.385(6) 4 ?
C17 C18 1.497(10) . ?
C18 O11 1.261(5) 4 ?
N1 C22 1.341(10) . ?
N1 C20 1.362(10) . ?
N1 C29 1.431(10) . ?
N2 C21 1.347(10) . ?
N2 C22 1.36(3) . ?
N2 C23 1.430(10) . ?
C20 C21 1.397(10) . ?
C23 C24 1.532(10) . ?
C24 C25 1.545(10) . ?
C25 C26 1.546(9) . ?
C26 C27 1.543(10) . ?
C27 C28 1.541(10) . ?
N1B C22B 1.351(10) . ?
N1B C20B 1.364(10) . ?
N1B C29B 1.441(10) . ?
N2B C22B 1.349(9) . ?
N2B C21B 1.368(9) . ?
N2B C23B 1.443(10) . ?
C20B C21B 1.402(10) . ?
C23B C24B 1.555(10) . ?
C24B C25B 1.543(9) . ?
C25B C26B 1.530(10) . ?
C26B C27B 1.535(10) . ?
C27B C28B 1.553(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O8 Eu1 O11 71.68(12) 4 1_565 ?
O8 Eu1 O4 135.57(12) 4 7_655 ?
O11 Eu1 O4 146.15(13) 1_565 7_655 ?
O8 Eu1 O10 73.38(12) 4 . ?
O11 Eu1 O10 138.61(12) 1_565 . ?
O4 Eu1 O10 75.22(12) 7_655 . ?
O8 Eu1 O1 112.88(12) 4 . ?
O11 Eu1 O1 75.07(12) 1_565 . ?
O4 Eu1 O1 74.89(13) 7_655 . ?
O10 Eu1 O1 140.38(13) . . ?
O8 Eu1 O9 67.16(11) 4 4 ?
O11 Eu1 O9 110.18(13) 1_565 4 ?
O4 Eu1 O9 74.89(12) 7_655 4 ?
O10 Eu1 O9 74.93(13) . 4 ?
O1 Eu1 O9 72.61(12) . 4 ?
O8 Eu1 O8 72.01(13) 4 . ?
O11 Eu1 O8 73.36(12) 1_565 . ?
O4 Eu1 O8 127.95(12) 7_655 . ?
O10 Eu1 O8 75.30(12) . . ?
O1 Eu1 O8 144.30(11) . . ?
O9 Eu1 O8 134.66(11) 4 . ?
O8 Eu1 O2 146.14(12) 4 . ?
O11 Eu1 O2 74.79(13) 1_565 . ?
O4 Eu1 O2 74.66(13) 7_655 . ?
O10 Eu1 O2 139.05(13) . . ?
O1 Eu1 O2 52.33(13) . . ?
O9 Eu1 O2 122.00(12) 4 . ?
O8 Eu1 O2 102.86(11) . . ?
O8 Eu1 O7 120.03(11) 4 . ?
O11 Eu1 O7 106.18(13) 1_565 . ?
O4 Eu1 O7 78.87(12) 7_655 . ?
O10 Eu1 O7 73.47(13) . . ?
O1 Eu1 O7 124.55(12) . . ?
O9 Eu1 O7 143.01(12) 4 . ?
O8 Eu1 O7 51.96(11) . . ?
O2 Eu1 O7 74.02(12) . . ?
O8 Eu1 C1 134.23(14) 4 . ?
O11 Eu1 C1 75.04(14) 1_565 . ?
O4 Eu1 C1 71.11(14) 7_655 . ?
O10 Eu1 C1 146.31(14) . . ?
O1 Eu1 C1 26.35(14) . . ?
O9 Eu1 C1 96.91(14) 4 . ?
O8 Eu1 C1 126.16(13) . . ?
O2 Eu1 C1 26.10(13) . . ?
O7 Eu1 C1 98.76(14) . . ?
O8 Eu1 C9 94.70(13) 4 . ?
O11 Eu1 C9 93.40(14) 1_565 . ?
O4 Eu1 C9 101.83(14) 7_655 . ?
O10 Eu1 C9 68.05(14) . . ?
O1 Eu1 C9 143.98(13) . . ?
O9 Eu1 C9 142.24(13) 4 . ?
O8 Eu1 C9 26.63(12) . . ?
O2 Eu1 C9 91.88(13) . . ?
O7 Eu1 C9 26.06(13) . . ?
C1 Eu1 C9 117.98(15) . . ?
O8 Eu1 Eu1 36.85(8) 4 4 ?
O11 Eu1 Eu1 69.23(9) 1_565 4 ?
O4 Eu1 Eu1 144.11(9) 7_655 4 ?
O10 Eu1 Eu1 69.54(8) . 4 ?
O1 Eu1 Eu1 139.21(9) . 4 ?
O9 Eu1 Eu1 101.67(8) 4 4 ?
O8 Eu1 Eu1 35.19(8) . 4 ?
O2 Eu1 Eu1 130.76(9) . 4 ?
O7 Eu1 Eu1 84.80(8) . 4 ?
C1 Eu1 Eu1 143.58(11) . 4 ?
C9 Eu1 Eu1 58.80(10) . 4 ?
C1 O1 Eu1 94.7(3) . . ?
C1 O2 Eu1 91.4(3) . . ?
C8 O4 Eu1 134.1(4) . 7_665 ?
C9 O7 Eu1 91.8(3) . . ?
C9 O8 Eu1 139.6(3) . 4 ?
C9 O8 Eu1 93.7(3) . . ?
Eu1 O8 Eu1 107.97(13) 4 . ?
C11 O9 Eu1 136.0(3) . 4 ?
C13 O10 Eu1 137.3(4) . . ?
C18 O11 Eu1 138.4(4) . 1_545 ?
O2 C1 O1 121.1(5) . . ?
O2 C1 C2 120.7(5) . . ?
O1 C1 C2 118.1(5) . . ?
O2 C1 Eu1 62.5(3) . . ?
O1 C1 Eu1 59.0(3) . . ?
C2 C1 Eu1 169.2(4) . . ?
C3 C2 C7 119.0(5) . . ?
C3 C2 C1 120.7(5) . . ?
C7 C2 C1 120.3(5) . . ?
C2 C3 C4 120.3(5) . . ?
C2 C3 O5 122.5(11) . . ?
C4 C3 O5 116.5(11) . . ?
C2 C3 O5B 122.0(16) . . ?
C4 C3 O5B 116.2(15) . . ?
C3 C4 C5 120.5(6) . . ?
C6 C5 C4 119.0(5) . . ?
C6 C5 C8 122.8(5) . . ?
C4 C5 C8 118.2(6) . . ?
C7 C6 C5 120.3(6) . . ?
C7 C6 O6 115.9(11) . . ?
C5 C6 O6 122.4(10) . . ?
C7 C6 O6B 117.1(11) . . ?
C5 C6 O6B 120.2(12) . . ?
C6 C7 C2 120.8(6) . . ?
O3 C8 O4 124.2(5) . . ?
O3 C8 C5 119.1(5) . . ?
O4 C8 C5 116.6(6) . . ?
O7 C9 O8 119.2(5) . . ?
O7 C9 C10 121.1(5) . . ?
O8 C9 C10 119.7(4) . . ?
O7 C9 Eu1 62.2(3) . . ?
O8 C9 Eu1 59.6(3) . . ?
C10 C9 Eu1 163.0(4) . . ?
C12 C10 C11 118.2(5) 5_556 . ?
C12 C10 C9 117.6(5) 5_556 . ?
C11 C10 C9 124.2(5) . . ?
O9 C11 C12 119.9(5) . . ?
O9 C11 C10 121.3(5) . . ?
C12 C11 C10 118.8(5) . . ?
C11 C12 C10 123.0(5) . 5_556 ?
O10 C13 O10 125.8(6) . 4 ?
O10 C13 C14 117.1(3) . . ?
O10 C13 C14 117.1(3) 4 . ?
C15 C14 C15 118.4(7) 4 . ?
C15 C14 C13 120.8(3) 4 . ?
C15 C14 C13 120.8(3) . . ?
O12A C15 C14 124.9(6) . . ?
O12A C15 C16 113.7(6) . . ?
C14 C15 C16 121.3(6) . . ?
O12B C16 C17 124.3(5) . . ?
O12B C16 C15 116.4(6) . . ?
C17 C16 C15 119.4(6) . . ?
C16 C17 C16 120.3(7) . 4 ?
C16 C17 C18 119.9(3) . . ?
C16 C17 C18 119.9(3) 4 . ?
O11 C18 O11 124.3(7) . 4 ?
O11 C18 C17 117.9(3) . . ?
O11 C18 C17 117.9(3) 4 . ?
C22 N1 C20 119.6(12) . . ?
C22 N1 C29 125(2) . . ?
C20 N1 C29 116(2) . . ?
C21 N2 C22 119.8(18) . . ?
C21 N2 C23 123(2) . . ?
C22 N2 C23 116(2) . . ?
N1 C20 C21 102.7(10) . . ?
N2 C21 C20 102.7(14) . . ?
N1 C22 N2 95.2(9) . . ?
N2 C23 C24 91.5(15) . . ?
C23 C24 C25 118.2(11) . . ?
C24 C25 C26 116.5(9) . . ?
C27 C26 C25 117.2(9) . . ?
C28 C27 C26 118.2(10) . . ?
C22B N1B C20B 118.7(11) . . ?
C22B N1B C29B 121.8(17) . . ?
C20B N1B C29B 119.5(17) . . ?
C22B N2B C21B 117.7(11) . . ?
C22B N2B C23B 124.9(17) . . ?
C21B N2B C23B 116.0(17) . . ?
N1B C20B C21B 102.5(9) . . ?
N2B C21B C20B 103.9(9) . . ?
N2B C22B N1B 97.3(9) . . ?
N2B C23B C24B 130.9(18) . . ?
C25B C24B C23B 117.2(10) . . ?
C26B C25B C24B 117.9(10) . . ?
C25B C26B C27B 118.9(11) . . ?
C26B C27B C28B 117.4(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5A O1 0.82 1.85 2.56(2) 144.8 .
O6 H6A O4 0.82 1.96 2.62(2) 137.7 .
O5B H5B O1 0.82 1.85 2.56(3) 144.7 .
O6B H6B O4 0.82 1.86 2.57(2) 144.5 .
O12A H12B O10 0.82 1.88 2.585(9) 142.6 .
O12B H12C O11 0.82 1.84 2.553(8) 144.4 .
O9 H9A O3 0.82 1.70 2.513(5) 172.1 6_556

_refine_diff_density_max         0.887
_refine_diff_density_min         -0.731
_refine_diff_density_rms         0.141

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1450973'
_audit_update_record             
;
2016-01-31 deposited with the CCDC.
2016-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H4 Ba O6'
_chemical_formula_sum            'C8 H4 Ba O6'
_chemical_formula_weight         333.45

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'
Ba Ba -0.3244 2.2819 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3881(4)
_cell_length_b                   7.4300(3)
_cell_length_c                   8.0377(4)
_cell_angle_alpha                69.771(4)
_cell_angle_beta                 67.998(5)
_cell_angle_gamma                79.288(4)
_cell_volume                     383.05(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    4719
_cell_measurement_theta_min      3.4080
_cell_measurement_theta_max      29.8050

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.891
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    5.190
_shelx_estimated_absorpt_T_min   0.682
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_T_min  0.86428
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_reflns_number            7330
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.370
_diffrn_reflns_theta_max         29.910
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2008
_reflns_number_gt                1858
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Diamond 3'
_computing_publication_material  'office 2007'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0166P)²+0.0857P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2008
_refine_ls_number_parameters     142
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0460
_refine_ls_wR_factor_gt          0.0438
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ba1 Ba 0.14870(3) 0.06970(2) 0.16316(2) 0.00602(6) Uani 1 1 d . . . . .
O1 O 0.5472(3) 0.0396(3) 0.1405(3) 0.0075(4) Uani 1 1 d . . . . .
O2 O 0.8087(3) 0.1989(3) 0.0610(3) 0.0077(4) Uani 1 1 d . . . . .
O3 O 0.1379(3) 0.8343(3) 0.5190(3) 0.0085(4) Uani 1 1 d . . . . .
O4 O 0.0066(3) 0.5785(3) 0.7525(3) 0.0089(4) Uani 1 1 d . . . . .
O5 O 0.0955(3) 0.2434(3) 0.7108(3) 0.0086(5) Uani 1 1 d D . . . .
H5 H 0.036(5) 0.329(3) 0.756(4) 0.010 Uiso 1 1 d D U . . .
O6 O 0.6859(3) 0.5736(3) 0.0566(3) 0.0074(4) Uani 1 1 d D . . . .
H6 H 0.763(4) 0.489(3) 0.022(4) 0.009 Uiso 1 1 d D U . . .
C1 C 0.6297(4) 0.1678(4) 0.1499(4) 0.0063(6) Uani 1 1 d . . . . .
C2 C 0.5069(4) 0.2925(4) 0.2695(4) 0.0062(6) Uani 1 1 d . . . . .
C3 C 0.3552(4) 0.2138(4) 0.4355(4) 0.0071(6) Uani 1 1 d . . . . .
H3A H 0.3342 0.0810 0.4739 0.008 Uiso 1 1 calc R U . . .
C4 C 0.2359(4) 0.3279(4) 0.5437(4) 0.0066(6) Uani 1 1 d . . . . .
C5 C 0.2592(4) 0.5262(4) 0.4815(4) 0.0069(6) Uani 1 1 d . . . . .
C6 C 0.4114(4) 0.6028(4) 0.3175(4) 0.0072(6) Uani 1 1 d . . . . .
H6A H 0.4290 0.7365 0.2758 0.009 Uiso 1 1 calc R U . . .
C7 C 0.5368(4) 0.4878(4) 0.2148(4) 0.0077(6) Uani 1 1 d . . . . .
C8 C 0.1273(4) 0.6554(4) 0.5909(4) 0.0066(6) 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
Ba1 O3 2.769(2) 1_545 ?
Ba1 O6 2.826(2) 2_665 ?
Ba1 O2 2.830(2) 1_455 ?
Ba1 O1 2.852(2) . ?
Ba1 O4 2.853(2) 2_566 ?
Ba1 O3 2.858(2) 2_566 ?
Ba1 O1 2.872(2) 2_655 ?
Ba1 O5 2.873(2) 2_556 ?
Ba1 O2 3.025(2) 2_655 ?
Ba1 C8 3.235(3) 2_566 ?
Ba1 C1 3.322(3) 2_655 ?
O1 C1 1.258(4) . ?
O1 Ba1 2.872(2) 2_655 ?
O2 C1 1.267(4) . ?
O2 Ba1 2.830(2) 1_655 ?
O2 Ba1 3.025(2) 2_655 ?
O3 C8 1.257(4) . ?
O3 Ba1 2.769(2) 1_565 ?
O3 Ba1 2.858(2) 2_566 ?
O4 C8 1.272(3) . ?
O4 Ba1 2.853(2) 2_566 ?
O5 C4 1.375(3) . ?
O5 Ba1 2.873(2) 2_556 ?
O5 H5 0.818(10) . ?
O6 C7 1.374(3) . ?
O6 Ba1 2.826(2) 2_665 ?
O6 H6 0.817(10) . ?
C1 C2 1.502(4) . ?
C1 Ba1 3.322(3) 2_655 ?
C2 C7 1.397(4) . ?
C2 C3 1.400(4) . ?
C3 C4 1.383(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.404(4) . ?
C5 C6 1.391(4) . ?
C5 C8 1.496(4) . ?
C6 C7 1.375(4) . ?
C6 H6A 0.9500 . ?
C8 Ba1 3.235(3) 2_566 ?

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 Ba1 O6 131.36(6) 1_545 2_665 ?
O3 Ba1 O2 122.81(6) 1_545 1_455 ?
O6 Ba1 O2 91.06(6) 2_665 1_455 ?
O3 Ba1 O1 77.34(6) 1_545 . ?
O6 Ba1 O1 70.70(6) 2_665 . ?
O2 Ba1 O1 159.55(6) 1_455 . ?
O3 Ba1 O4 99.35(6) 1_545 2_566 ?
O6 Ba1 O4 56.49(6) 2_665 2_566 ?
O2 Ba1 O4 71.16(6) 1_455 2_566 ?
O1 Ba1 O4 104.23(6) . 2_566 ?
O3 Ba1 O3 61.95(7) 1_545 2_566 ?
O6 Ba1 O3 101.53(6) 2_665 2_566 ?
O2 Ba1 O3 75.05(6) 1_455 2_566 ?
O1 Ba1 O3 116.68(6) . 2_566 ?
O4 Ba1 O3 45.77(6) 2_566 2_566 ?
O3 Ba1 O1 114.56(6) 1_545 2_655 ?
O6 Ba1 O1 79.48(6) 2_665 2_655 ?
O2 Ba1 O1 108.73(6) 1_455 2_655 ?
O1 Ba1 O1 60.00(7) . 2_655 ?
O4 Ba1 O1 135.74(6) 2_566 2_655 ?
O3 Ba1 O1 176.12(6) 2_566 2_655 ?
O3 Ba1 O5 68.97(6) 1_545 2_556 ?
O6 Ba1 O5 158.80(6) 2_665 2_556 ?
O2 Ba1 O5 69.63(6) 1_455 2_556 ?
O1 Ba1 O5 126.43(6) . 2_556 ?
O4 Ba1 O5 121.05(6) 2_566 2_556 ?
O3 Ba1 O5 82.37(6) 2_566 2_556 ?
O1 Ba1 O5 98.05(6) 2_655 2_556 ?
O3 Ba1 O2 105.60(6) 1_545 2_655 ?
O6 Ba1 O2 114.05(5) 2_665 2_655 ?
O2 Ba1 O2 81.07(6) 1_455 2_655 ?
O1 Ba1 O2 97.65(6) . 2_655 ?
O4 Ba1 O2 149.83(6) 2_566 2_655 ?
O3 Ba1 O2 137.19(6) 2_566 2_655 ?
O1 Ba1 O2 44.19(6) 2_655 2_655 ?
O5 Ba1 O2 55.93(5) 2_556 2_655 ?
O3 Ba1 C8 80.64(7) 1_545 2_566 ?
O6 Ba1 C8 79.24(7) 2_665 2_566 ?
O2 Ba1 C8 70.97(7) 1_455 2_566 ?
O1 Ba1 C8 112.83(7) . 2_566 ?
O4 Ba1 C8 23.04(6) 2_566 2_566 ?
O3 Ba1 C8 22.75(6) 2_566 2_566 ?
O1 Ba1 C8 158.70(7) 2_655 2_566 ?
O5 Ba1 C8 101.53(7) 2_556 2_566 ?
O2 Ba1 C8 149.48(7) 2_655 2_566 ?
O3 Ba1 C1 109.97(6) 1_545 2_655 ?
O6 Ba1 C1 97.88(6) 2_665 2_655 ?
O2 Ba1 C1 96.68(7) 1_455 2_655 ?
O1 Ba1 C1 77.46(7) . 2_655 ?
O4 Ba1 C1 150.10(6) 2_566 2_655 ?
O3 Ba1 C1 158.96(7) 2_566 2_655 ?
O1 Ba1 C1 21.93(7) 2_655 2_655 ?
O5 Ba1 C1 76.60(6) 2_556 2_655 ?
O2 Ba1 C1 22.40(6) 2_655 2_655 ?
C8 Ba1 C1 167.13(7) 2_566 2_655 ?
O3 Ba1 Ba1 121.81(4) 1_545 2 ?
O6 Ba1 Ba1 106.78(4) 2_665 2 ?
O2 Ba1 Ba1 42.17(4) 1_455 2 ?
O1 Ba1 Ba1 133.32(4) . 2 ?
O4 Ba1 Ba1 112.47(4) 2_566 2 ?
O3 Ba1 Ba1 109.54(4) 2_566 2 ?
O1 Ba1 Ba1 73.56(4) 2_655 2 ?
O5 Ba1 Ba1 52.99(4) 2_556 2 ?
O2 Ba1 Ba1 38.90(4) 2_655 2 ?
C8 Ba1 Ba1 112.22(5) 2_566 2 ?
C1 Ba1 Ba1 56.33(5) 2_655 2 ?
C1 O1 Ba1 124.62(18) . . ?
C1 O1 Ba1 99.58(17) . 2_655 ?
Ba1 O1 Ba1 120.00(7) . 2_655 ?
C1 O2 Ba1 132.50(17) . 1_655 ?
C1 O2 Ba1 92.07(18) . 2_655 ?
Ba1 O2 Ba1 98.93(6) 1_655 2_655 ?
C8 O3 Ba1 130.58(19) . 1_565 ?
C8 O3 Ba1 95.73(17) . 2_566 ?
Ba1 O3 Ba1 118.05(7) 1_565 2_566 ?
C8 O4 Ba1 95.60(17) . 2_566 ?
C4 O5 Ba1 134.16(18) . 2_556 ?
C4 O5 H5 107(2) . . ?
Ba1 O5 H5 111(2) 2_556 . ?
C7 O6 Ba1 143.09(18) . 2_665 ?
C7 O6 H6 108(2) . . ?
Ba1 O6 H6 108(2) 2_665 . ?
O1 C1 O2 123.4(3) . . ?
O1 C1 C2 117.8(3) . . ?
O2 C1 C2 118.8(3) . . ?
O1 C1 Ba1 58.49(15) . 2_655 ?
O2 C1 Ba1 65.53(16) . 2_655 ?
C2 C1 Ba1 169.6(2) . 2_655 ?
C7 C2 C3 119.3(3) . . ?
C7 C2 C1 121.1(3) . . ?
C3 C2 C1 119.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3A 119.8 . . ?
C2 C3 H3A 119.8 . . ?
O5 C4 C3 118.7(3) . . ?
O5 C4 C5 121.4(3) . . ?
C3 C4 C5 119.9(3) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 C8 119.5(3) . . ?
C4 C5 C8 121.3(3) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
O6 C7 C6 117.5(3) . . ?
O6 C7 C2 122.4(3) . . ?
C6 C7 C2 120.1(3) . . ?
O3 C8 O4 122.8(3) . . ?
O3 C8 C5 119.1(2) . . ?
O4 C8 C5 118.1(3) . . ?
O3 C8 Ba1 61.52(15) . 2_566 ?
O4 C8 Ba1 61.36(15) . 2_566 ?
C5 C8 Ba1 178.0(2) . 2_566 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ba1 O1 C1 O2 -146.8(2) . . . . ?
Ba1 O1 C1 O2 -9.6(3) 2_655 . . . ?
Ba1 O1 C1 C2 31.7(3) . . . . ?
Ba1 O1 C1 C2 168.8(2) 2_655 . . . ?
Ba1 O1 C1 Ba1 -137.11(19) . . . 2_655 ?
Ba1 O2 C1 O1 -95.1(3) 1_655 . . . ?
Ba1 O2 C1 O1 9.0(3) 2_655 . . . ?
Ba1 O2 C1 C2 86.5(3) 1_655 . . . ?
Ba1 O2 C1 C2 -169.4(2) 2_655 . . . ?
Ba1 O2 C1 Ba1 -104.1(2) 1_655 . . 2_655 ?
O1 C1 C2 C7 -142.9(3) . . . . ?
O2 C1 C2 C7 35.7(4) . . . . ?
Ba1 C1 C2 C7 -76.6(12) 2_655 . . . ?
O1 C1 C2 C3 34.9(4) . . . . ?
O2 C1 C2 C3 -146.6(3) . . . . ?
Ba1 C1 C2 C3 101.1(11) 2_655 . . . ?
C7 C2 C3 C4 0.2(5) . . . . ?
C1 C2 C3 C4 -177.6(3) . . . . ?
Ba1 O5 C4 C3 -34.5(4) 2_556 . . . ?
Ba1 O5 C4 C5 145.1(2) 2_556 . . . ?
C2 C3 C4 O5 -176.5(3) . . . . ?
C2 C3 C4 C5 3.8(5) . . . . ?
O5 C4 C5 C6 175.9(3) . . . . ?
C3 C4 C5 C6 -4.4(5) . . . . ?
O5 C4 C5 C8 -2.3(5) . . . . ?
C3 C4 C5 C8 177.4(3) . . . . ?
C4 C5 C6 C7 0.9(5) . . . . ?
C8 C5 C6 C7 179.2(3) . . . . ?
Ba1 O6 C7 C6 -0.4(5) 2_665 . . . ?
Ba1 O6 C7 C2 177.8(2) 2_665 . . . ?
C5 C6 C7 O6 -178.7(3) . . . . ?
C5 C6 C7 C2 3.1(5) . . . . ?
C3 C2 C7 O6 178.2(3) . . . . ?
C1 C2 C7 O6 -4.1(5) . . . . ?
C3 C2 C7 C6 -3.7(5) . . . . ?
C1 C2 C7 C6 174.1(3) . . . . ?
Ba1 O3 C8 O4 -131.8(2) 1_565 . . . ?
Ba1 O3 C8 O4 3.3(3) 2_566 . . . ?
Ba1 O3 C8 C5 47.1(4) 1_565 . . . ?
Ba1 O3 C8 C5 -177.8(2) 2_566 . . . ?
Ba1 O3 C8 Ba1 -135.1(2) 1_565 . . 2_566 ?
Ba1 O4 C8 O3 -3.3(3) 2_566 . . . ?
Ba1 O4 C8 C5 177.8(2) 2_566 . . . ?
C6 C5 C8 O3 10.4(4) . . . . ?
C4 C5 C8 O3 -171.4(3) . . . . ?
C6 C5 C8 O4 -170.7(3) . . . . ?
C4 C5 C8 O4 7.6(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O2 0.818(10) 2.37(3) 2.769(3) 111(3) 1_456
O5 H5 O4 0.818(10) 1.816(19) 2.559(3) 150(3) .
O6 H6 O2 0.817(10) 2.05(2) 2.756(3) 145(3) .
O6 H6 O4 0.817(10) 2.21(3) 2.687(3) 117(3) 1_654
C3 H3A O3 0.95 2.39 3.247(4) 149.3 1_545
C6 H6A O1 0.95 2.31 3.242(4) 166.5 1_565
O5 H5 O2 0.818(10) 2.37(3) 2.769(3) 111(3) 1_456
O5 H5 O4 0.818(10) 1.816(19) 2.559(3) 150(3) .
O6 H6 O2 0.817(10) 2.05(2) 2.756(3) 145(3) .
O6 H6 O4 0.817(10) 2.21(3) 2.687(3) 117(3) 1_654
C3 H3A O3 0.95 2.39 3.247(4) 149.3 1_545
C6 H6A O1 0.95 2.31 3.242(4) 166.5 1_565

_refine_diff_density_max         1.438
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.177

_shelxl_version_number           2013-2

