# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_audit_block_doi                 10.5517/cc1382dv
_database_code_depnum_ccdc_archive 'CCDC 1020656'
_audit_update_record             
;
2014-08-22 deposited with the CCDC.
2015-01-19 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 H16 Eu2 N2 O18'
_chemical_formula_weight         828.23

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   6.6723(9)
_cell_length_b                   8.3982(13)
_cell_length_c                   10.312(2)
_cell_angle_alpha                75.470(16)
_cell_angle_beta                 71.695(15)
_cell_angle_gamma                88.038(13)
_cell_volume                     530.44(15)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    639
_cell_measurement_theta_min      3.2094
_cell_measurement_theta_max      28.8162

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             396
_exptl_absorpt_coefficient_mu    5.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1990
_exptl_absorpt_correction_T_max  0.2679
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.0971
_diffrn_standards_number         1244
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3924
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2084
_reflns_number_gt                1978
_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)+(0.0264P)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         2084
_refine_ls_number_parameters     172
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0245
_refine_ls_wR_factor_ref         0.0579
_refine_ls_wR_factor_gt          0.0572
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.052
_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 0.27372(3) 0.65372(2) 0.68174(2) 0.00445(8) Uani 1 1 d . . .
O4 O 0.6107(5) 0.8080(4) 0.5278(3) 0.0085(6) Uani 1 1 d . . .
O3 O 0.2867(5) 0.7271(4) 0.4366(3) 0.0088(6) Uani 1 1 d . . .
O6 O 0.0192(5) 0.7002(4) 0.8945(3) 0.0071(6) Uani 1 1 d . . .
O1 O 0.4702(5) 0.7005(4) -0.1564(3) 0.0087(6) Uani 1 1 d . . .
O2 O 0.4446(5) 0.5249(4) 0.3434(3) 0.0095(6) Uani 1 1 d . . .
O5 O 0.7464(5) 1.0465(4) 0.3704(3) 0.0076(6) Uani 1 1 d . . .
O8 O -0.0842(5) 0.7046(4) 0.6677(4) 0.0173(8) Uani 1 1 d . . .
H8A H -0.1176 0.7269 0.5925 0.026 Uiso 1 1 d R . .
H8B H -0.1952 0.7009 0.7370 0.026 Uiso 1 1 d R . .
N1 N 0.3942(5) 0.7666(4) -0.0451(4) 0.0060(7) Uani 1 1 d . . .
O9 O 0.1419(5) 0.4129(4) 0.6199(3) 0.0184(8) Uani 1 1 d . . .
H9A H 0.2396 0.3684 0.5670 0.028 Uiso 1 1 d R . .
H9B H 0.0774 0.3383 0.6928 0.028 Uiso 1 1 d R . .
C7 C 0.6037(6) 0.9577(5) 0.4702(4) 0.0043(8) Uani 1 1 d U . .
O7 O -0.1593(5) 0.5973(4) 1.1232(3) 0.0092(6) Uani 1 1 d . . .
C2 C 0.3311(7) 0.7511(6) 0.1972(5) 0.0086(9) Uani 1 1 d . . .
C3 C 0.2346(7) 0.9002(5) 0.1823(5) 0.0086(9) Uani 1 1 d . . .
H3 H 0.1779 0.9461 0.2609 0.010 Uiso 1 1 calc R . .
C5 C 0.3031(6) 0.9135(5) -0.0625(5) 0.0078(9) Uani 1 1 d . . .
H5 H 0.2949 0.9696 -0.1528 0.009 Uiso 1 1 calc R . .
C6 C 0.3557(7) 0.6589(5) 0.3364(5) 0.0080(9) Uani 1 1 d . . .
C1 C 0.4077(6) 0.6851(5) 0.0820(5) 0.0065(8) Uani 1 1 d . . .
H1 H 0.4705 0.5814 0.0925 0.008 Uiso 1 1 calc R . .
C8 C -0.0396(7) 0.5867(5) 1.0046(5) 0.0066(9) Uani 1 1 d . . .
C4 C 0.2224(7) 0.9816(5) 0.0500(5) 0.0090(9) Uani 1 1 d U . .
H4 H 0.1579 1.0845 0.0375 0.011 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 O2 2.355(3) 2_666 ?
Eu1 O3 2.421(3) . ?
Eu1 O6 2.428(3) . ?
Eu1 O5 2.447(3) 2_676 ?
Eu1 O8 2.454(3) . ?
Eu1 O7 2.468(3) 2_567 ?
Eu1 O4 2.486(3) . ?
Eu1 O9 2.528(3) . ?
Eu1 O1 2.530(3) 1_556 ?
Eu1 C8 3.246(5) . ?
Eu1 C7 3.254(4) 2_676 ?
O4 C7 1.255(5) . ?
O3 C6 1.260(5) . ?
O6 C8 1.246(5) . ?
O1 N1 1.348(4) . ?
O1 Eu1 2.530(3) 1_554 ?
O2 C6 1.251(5) . ?
O2 Eu1 2.355(3) 2_666 ?
O5 C7 1.253(5) . ?
O5 Eu1 2.447(3) 2_676 ?
O8 H8A 0.8477 . ?
O8 H8B 0.8479 . ?
N1 C1 1.347(6) . ?
N1 C5 1.352(5) . ?
O9 H9A 0.8512 . ?
O9 H9B 0.8496 . ?
C7 C7 1.554(8) 2_676 ?
C7 Eu1 3.254(4) 2_676 ?
O7 C8 1.256(5) . ?
O7 Eu1 2.468(3) 2_567 ?
C2 C1 1.382(6) . ?
C2 C3 1.385(6) . ?
C2 C6 1.506(6) . ?
C3 C4 1.391(6) . ?
C3 H3 0.9500 . ?
C5 C4 1.372(6) . ?
C5 H5 0.9500 . ?
C1 H1 0.9500 . ?
C8 C8 1.547(8) 2_567 ?
C4 H4 0.9500 . ?

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 O3 96.64(10) 2_666 . ?
O2 Eu1 O6 129.67(10) 2_666 . ?
O3 Eu1 O6 132.74(10) . . ?
O2 Eu1 O5 133.79(10) 2_666 2_676 ?
O3 Eu1 O5 77.17(10) . 2_676 ?
O6 Eu1 O5 76.28(10) . 2_676 ?
O2 Eu1 O8 146.27(11) 2_666 . ?
O3 Eu1 O8 70.62(11) . . ?
O6 Eu1 O8 65.20(10) . . ?
O5 Eu1 O8 75.27(11) 2_676 . ?
O2 Eu1 O7 72.59(10) 2_666 2_567 ?
O3 Eu1 O7 134.18(10) . 2_567 ?
O6 Eu1 O7 65.99(10) . 2_567 ?
O5 Eu1 O7 141.75(10) 2_676 2_567 ?
O8 Eu1 O7 93.69(11) . 2_567 ?
O2 Eu1 O4 69.44(11) 2_666 . ?
O3 Eu1 O4 68.94(10) . . ?
O6 Eu1 O4 130.10(9) . . ?
O5 Eu1 O4 65.62(10) 2_676 . ?
O8 Eu1 O4 128.38(11) . . ?
O7 Eu1 O4 137.77(10) 2_567 . ?
O2 Eu1 O9 75.15(11) 2_666 . ?
O3 Eu1 O9 69.63(11) . . ?
O6 Eu1 O9 109.32(10) . . ?
O5 Eu1 O9 138.75(10) 2_676 . ?
O8 Eu1 O9 71.15(11) . . ?
O7 Eu1 O9 64.55(10) 2_567 . ?
O4 Eu1 O9 120.53(10) . . ?
O2 Eu1 O1 74.15(9) 2_666 1_556 ?
O3 Eu1 O1 141.94(10) . 1_556 ?
O6 Eu1 O1 71.21(10) . 1_556 ?
O5 Eu1 O1 83.18(9) 2_676 1_556 ?
O8 Eu1 O1 134.68(10) . 1_556 ?
O7 Eu1 O1 79.20(10) 2_567 1_556 ?
O4 Eu1 O1 73.32(10) . 1_556 ?
O9 Eu1 O1 137.94(11) . 1_556 ?
O2 Eu1 C8 112.75(10) 2_666 . ?
O3 Eu1 C8 144.11(10) . . ?
O6 Eu1 C8 19.27(10) . . ?
O5 Eu1 C8 95.15(10) 2_676 . ?
O8 Eu1 C8 73.52(10) . . ?
O7 Eu1 C8 46.82(10) 2_567 . ?
O4 Eu1 C8 139.67(9) . . ?
O9 Eu1 C8 97.59(11) . . ?
O1 Eu1 C8 69.25(10) 1_556 . ?
O2 Eu1 C7 116.32(11) 2_666 2_676 ?
O3 Eu1 C7 67.10(10) . 2_676 ?
O6 Eu1 C7 95.01(10) . 2_676 ?
O5 Eu1 C7 19.57(10) 2_676 2_676 ?
O8 Eu1 C7 88.10(11) . 2_676 ?
O7 Eu1 C7 157.74(9) 2_567 2_676 ?
O4 Eu1 C7 46.97(10) . 2_676 ?
O9 Eu1 C7 136.16(10) . 2_676 ?
O1 Eu1 C7 83.78(10) 1_556 2_676 ?
C8 Eu1 C7 113.32(10) . 2_676 ?
C7 O4 Eu1 118.1(3) . . ?
C6 O3 Eu1 134.0(3) . . ?
C8 O6 Eu1 120.7(3) . . ?
N1 O1 Eu1 126.7(2) . 1_554 ?
C6 O2 Eu1 157.5(3) . 2_666 ?
C7 O5 Eu1 119.6(3) . 2_676 ?
Eu1 O8 H8A 125.5 . . ?
Eu1 O8 H8B 125.9 . . ?
H8A O8 H8B 108.6 . . ?
C1 N1 O1 119.7(3) . . ?
C1 N1 C5 120.9(3) . . ?
O1 N1 C5 119.4(3) . . ?
Eu1 O9 H9A 113.4 . . ?
Eu1 O9 H9B 112.2 . . ?
H9A O9 H9B 107.8 . . ?
O5 C7 O4 127.0(4) . . ?
O5 C7 C7 116.5(5) . 2_676 ?
O4 C7 C7 116.5(5) . 2_676 ?
O5 C7 Eu1 40.84(19) . 2_676 ?
O4 C7 Eu1 163.5(3) . 2_676 ?
C7 C7 Eu1 76.8(3) 2_676 2_676 ?
C8 O7 Eu1 119.8(3) . 2_567 ?
C1 C2 C3 119.5(4) . . ?
C1 C2 C6 119.0(4) . . ?
C3 C2 C6 121.5(4) . . ?
C2 C3 C4 118.7(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N1 C5 C4 120.2(4) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O2 C6 O3 125.4(4) . . ?
O2 C6 C2 118.6(4) . . ?
O3 C6 C2 116.0(4) . . ?
N1 C1 C2 120.6(4) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
O6 C8 O7 126.8(4) . . ?
O6 C8 C8 117.3(5) . 2_567 ?
O7 C8 C8 115.8(5) . 2_567 ?
O6 C8 Eu1 40.0(2) . . ?
O7 C8 Eu1 166.4(3) . . ?
C8 C8 Eu1 77.4(3) 2_567 . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?

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
O2 Eu1 O4 C7 175.2(3) 2_666 . . . ?
O3 Eu1 O4 C7 69.1(3) . . . . ?
O6 Eu1 O4 C7 -59.7(3) . . . . ?
O5 Eu1 O4 C7 -15.9(3) 2_676 . . . ?
O8 Eu1 O4 C7 28.5(3) . . . . ?
O7 Eu1 O4 C7 -157.5(2) 2_567 . . . ?
O9 Eu1 O4 C7 117.8(3) . . . . ?
O1 Eu1 O4 C7 -105.9(3) 1_556 . . . ?
C8 Eu1 O4 C7 -83.5(3) . . . . ?
C7 Eu1 O4 C7 -8.7(3) 2_676 . . . ?
O2 Eu1 O3 C6 23.4(4) 2_666 . . . ?
O6 Eu1 O3 C6 -145.9(4) . . . . ?
O5 Eu1 O3 C6 156.9(4) 2_676 . . . ?
O8 Eu1 O3 C6 -124.4(4) . . . . ?
O7 Eu1 O3 C6 -48.7(4) 2_567 . . . ?
O4 Eu1 O3 C6 88.3(4) . . . . ?
O9 Eu1 O3 C6 -48.0(4) . . . . ?
O1 Eu1 O3 C6 96.1(4) 1_556 . . . ?
C8 Eu1 O3 C6 -122.2(4) . . . . ?
C7 Eu1 O3 C6 139.2(4) 2_676 . . . ?
O2 Eu1 O6 C8 -31.8(3) 2_666 . . . ?
O3 Eu1 O6 C8 134.4(3) . . . . ?
O5 Eu1 O6 C8 -168.1(3) 2_676 . . . ?
O8 Eu1 O6 C8 112.0(3) . . . . ?
O7 Eu1 O6 C8 5.5(3) 2_567 . . . ?
O4 Eu1 O6 C8 -127.7(3) . . . . ?
O9 Eu1 O6 C8 54.6(3) . . . . ?
O1 Eu1 O6 C8 -80.7(3) 1_556 . . . ?
C7 Eu1 O6 C8 -162.4(3) 2_676 . . . ?
Eu1 O1 N1 C1 127.0(3) 1_554 . . . ?
Eu1 O1 N1 C5 -52.3(5) 1_554 . . . ?
Eu1 O5 C7 O4 -164.7(3) 2_676 . . . ?
Eu1 O5 C7 C7 14.8(5) 2_676 . . 2_676 ?
Eu1 O4 C7 O5 -165.5(3) . . . . ?
Eu1 O4 C7 C7 15.0(5) . . . 2_676 ?
Eu1 O4 C7 Eu1 157.0(8) . . . 2_676 ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C6 C2 C3 C4 178.2(4) . . . . ?
C1 N1 C5 C4 -0.1(6) . . . . ?
O1 N1 C5 C4 179.1(4) . . . . ?
Eu1 O2 C6 O3 -97.5(8) 2_666 . . . ?
Eu1 O2 C6 C2 81.1(8) 2_666 . . . ?
Eu1 O3 C6 O2 -1.3(7) . . . . ?
Eu1 O3 C6 C2 -179.8(3) . . . . ?
C1 C2 C6 O2 -0.1(6) . . . . ?
C3 C2 C6 O2 -179.9(4) . . . . ?
C1 C2 C6 O3 178.5(4) . . . . ?
C3 C2 C6 O3 -1.2(6) . . . . ?
O1 N1 C1 C2 179.8(4) . . . . ?
C5 N1 C1 C2 -0.9(6) . . . . ?
C3 C2 C1 N1 1.7(6) . . . . ?
C6 C2 C1 N1 -178.0(4) . . . . ?
Eu1 O6 C8 O7 175.2(3) . . . . ?
Eu1 O6 C8 C8 -5.6(6) . . . 2_567 ?
Eu1 O7 C8 O6 174.8(3) 2_567 . . . ?
Eu1 O7 C8 C8 -4.4(6) 2_567 . . 2_567 ?
Eu1 O7 C8 Eu1 -172.0(10) 2_567 . . . ?
O2 Eu1 C8 O6 153.9(3) 2_666 . . . ?
O3 Eu1 C8 O6 -63.6(4) . . . . ?
O5 Eu1 C8 O6 11.6(3) 2_676 . . . ?
O8 Eu1 C8 O6 -61.4(3) . . . . ?
O7 Eu1 C8 O6 -173.1(3) 2_567 . . . ?
O4 Eu1 C8 O6 69.3(3) . . . . ?
O9 Eu1 C8 O6 -129.1(3) . . . . ?
O1 Eu1 C8 O6 92.3(3) 1_556 . . . ?
C7 Eu1 C8 O6 19.1(3) 2_676 . . . ?
O2 Eu1 C8 O7 137.5(12) 2_666 . . . ?
O3 Eu1 C8 O7 -80.0(12) . . . . ?
O6 Eu1 C8 O7 -16.4(10) . . . . ?
O5 Eu1 C8 O7 -4.8(12) 2_676 . . . ?
O8 Eu1 C8 O7 -77.8(12) . . . . ?
O7 Eu1 C8 O7 170.5(12) 2_567 . . . ?
O4 Eu1 C8 O7 52.9(12) . . . . ?
O9 Eu1 C8 O7 -145.5(12) . . . . ?
O1 Eu1 C8 O7 75.9(12) 1_556 . . . ?
C7 Eu1 C8 O7 2.7(12) 2_676 . . . ?
O2 Eu1 C8 C8 -31.2(3) 2_666 . . 2_567 ?
O3 Eu1 C8 C8 111.3(3) . . . 2_567 ?
O6 Eu1 C8 C8 174.9(5) . . . 2_567 ?
O5 Eu1 C8 C8 -173.5(3) 2_676 . . 2_567 ?
O8 Eu1 C8 C8 113.5(3) . . . 2_567 ?
O7 Eu1 C8 C8 1.8(2) 2_567 . . 2_567 ?
O4 Eu1 C8 C8 -115.8(3) . . . 2_567 ?
O9 Eu1 C8 C8 45.8(3) . . . 2_567 ?
O1 Eu1 C8 C8 -92.8(3) 1_556 . . 2_567 ?
C7 Eu1 C8 C8 -166.0(3) 2_676 . . 2_567 ?
N1 C5 C4 C3 0.3(6) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.779
_refine_diff_density_min         -1.478
_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_2327
_database_code_depnum_ccdc_archive 'CCDC 1023399'
_audit_update_record             
;
2014-09-09 deposited with the CCDC.
2015-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H20 N4 O18 Tb2'
_chemical_formula_weight         994.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.2954(4)
_cell_length_b                   9.7473(5)
_cell_length_c                   9.8872(6)
_cell_angle_alpha                101.508(5)
_cell_angle_beta                 108.666(5)
_cell_angle_gamma                101.022(4)
_cell_volume                     713.62(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    102.5
_cell_measurement_reflns_used    3747
_cell_measurement_theta_min      2.9775
_cell_measurement_theta_max      29.3516

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             478
_exptl_absorpt_coefficient_mu    5.013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4338
_exptl_absorpt_correction_T_max  0.6340
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      102.5
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5412
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0531
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2800
_reflns_number_gt                2650
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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)+(0.0255P)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         2800
_refine_ls_number_parameters     226
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.094
_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
Tb1 Tb 0.40030(2) 0.65347(2) 0.16755(2) 0.00500(8) Uani 1 1 d . . .
N1 N 0.2306(5) -0.0552(4) 0.1543(4) 0.0106(8) Uani 1 1 d . . .
N2 N 0.3661(5) 0.6693(4) 0.4936(4) 0.0070(8) Uani 1 1 d . . .
C1 C 0.4200(5) 0.2855(5) 0.0735(5) 0.0061(9) Uani 1 1 d U . .
C2 C 0.3286(5) 0.1840(5) 0.1391(5) 0.0072(9) Uani 1 1 d . . .
C3 C 0.2660(6) 0.2377(5) 0.2481(5) 0.0107(10) Uani 1 1 d . . .
H3 H 0.2744 0.3364 0.2776 0.013 Uiso 1 1 calc R . .
C4 C 0.1912(6) 0.1418(5) 0.3117(5) 0.0134(10) Uani 1 1 d . . .
H4 H 0.1538 0.1763 0.3878 0.016 Uiso 1 1 calc R . .
C5 C 0.1724(6) -0.0052(5) 0.2616(5) 0.0136(10) Uani 1 1 d . . .
H5 H 0.1193 -0.0700 0.3024 0.016 Uiso 1 1 calc R . .
C6 C 0.3095(6) 0.0356(5) 0.0938(5) 0.0097(9) Uani 1 1 d . . .
H6 H 0.3515 -0.0011 0.0216 0.012 Uiso 1 1 calc R . .
C7 C 0.2965(6) 1.0191(5) 0.6662(5) 0.0093(9) Uani 1 1 d . . .
C8 C 0.2832(5) 0.8585(5) 0.6210(5) 0.0077(9) Uani 1 1 d . . .
C9 C 0.1921(5) 0.7591(5) 0.6741(5) 0.0092(9) Uani 1 1 d . . .
H9 H 0.1323 0.7890 0.7346 0.011 Uiso 1 1 calc R . .
C10 C 0.1935(5) 0.6152(5) 0.6340(5) 0.0088(9) Uani 1 1 d . . .
H10 H 0.1338 0.5473 0.6678 0.011 Uiso 1 1 calc R . .
C11 C 0.2821(6) 0.5715(5) 0.5448(5) 0.0082(9) Uani 1 1 d . . .
H11 H 0.2842 0.4748 0.5198 0.010 Uiso 1 1 calc R . .
C12 C 0.3690(5) 0.8107(5) 0.5303(5) 0.0070(9) Uani 1 1 d . . .
H12 H 0.4291 0.8763 0.4944 0.008 Uiso 1 1 calc R . .
C13 C -0.0122(5) 0.5069(4) 0.0755(5) 0.0060(9) Uani 1 1 d . . .
O1 O 0.2089(4) -0.1967(3) 0.1071(4) 0.0132(7) Uani 1 1 d . . .
O2 O 0.4920(4) 0.2320(3) -0.0116(4) 0.0107(7) Uani 1 1 d . . .
O3 O 0.4206(4) 0.4167(3) 0.1077(3) 0.0106(7) Uani 1 1 d . . .
O4 O 0.4548(4) 0.6271(3) 0.4090(3) 0.0084(6) Uani 1 1 d U . .
O5 O 0.4394(4) 1.1057(3) 0.6798(3) 0.0085(6) Uani 1 1 d . . .
O6 O 0.1680(4) 1.0531(3) 0.6898(4) 0.0183(8) Uani 1 1 d . . .
O7 O -0.1692(4) 0.4741(3) 0.0693(3) 0.0082(6) Uani 1 1 d . . .
O8 O 0.1258(4) 0.5467(3) 0.1906(3) 0.0086(7) Uani 1 1 d . . .
O9 O 0.7110(4) 0.6597(3) 0.2539(3) 0.0098(7) Uani 1 1 d . . .
H9A H 0.7330 0.5982 0.1938 0.015 Uiso 1 1 d R . .
H9B H 0.7735 0.7447 0.2660 0.015 Uiso 1 1 d R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O3 2.318(3) . ?
Tb1 O4 2.360(3) . ?
Tb1 O2 2.369(3) 2_665 ?
Tb1 O1 2.374(3) 1_565 ?
Tb1 O5 2.380(3) 2_676 ?
Tb1 O7 2.399(3) 2_565 ?
Tb1 O8 2.417(3) . ?
Tb1 O9 2.426(3) . ?
N1 O1 1.322(5) . ?
N1 C5 1.345(6) . ?
N1 C6 1.345(6) . ?
N2 O4 1.334(5) . ?
N2 C11 1.347(6) . ?
N2 C12 1.347(5) . ?
C1 O3 1.254(5) . ?
C1 O2 1.266(5) . ?
C1 C2 1.503(6) . ?
C2 C6 1.388(6) . ?
C2 C3 1.393(6) . ?
C3 C4 1.384(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O6 1.251(5) . ?
C7 O5 1.267(5) . ?
C7 C8 1.512(6) . ?
C8 C12 1.377(6) . ?
C8 C9 1.401(6) . ?
C9 C10 1.382(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(6) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 O8 1.256(5) . ?
C13 O7 1.259(5) . ?
C13 C13 1.552(9) 2_565 ?
O1 Tb1 2.374(3) 1_545 ?
O2 Tb1 2.369(3) 2_665 ?
O5 Tb1 2.380(3) 2_676 ?
O7 Tb1 2.399(3) 2_565 ?
O9 H9A 0.8461 . ?
O9 H9B 0.8528 . ?

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 Tb1 O4 84.86(11) . . ?
O3 Tb1 O2 105.64(11) . 2_665 ?
O4 Tb1 O2 147.01(10) . 2_665 ?
O3 Tb1 O1 143.13(10) . 1_565 ?
O4 Tb1 O1 112.58(11) . 1_565 ?
O2 Tb1 O1 77.76(11) 2_665 1_565 ?
O3 Tb1 O5 143.48(10) . 2_676 ?
O4 Tb1 O5 77.79(11) . 2_676 ?
O2 Tb1 O5 75.55(11) 2_665 2_676 ?
O1 Tb1 O5 73.36(10) 1_565 2_676 ?
O3 Tb1 O7 72.58(10) . 2_565 ?
O4 Tb1 O7 132.80(11) . 2_565 ?
O2 Tb1 O7 79.93(11) 2_665 2_565 ?
O1 Tb1 O7 71.97(10) 1_565 2_565 ?
O5 Tb1 O7 140.90(10) 2_676 2_565 ?
O3 Tb1 O8 85.38(10) . . ?
O4 Tb1 O8 69.74(10) . . ?
O2 Tb1 O8 140.93(10) 2_665 . ?
O1 Tb1 O8 72.06(11) 1_565 . ?
O5 Tb1 O8 117.22(10) 2_676 . ?
O7 Tb1 O8 67.63(10) 2_565 . ?
O3 Tb1 O9 71.68(10) . . ?
O4 Tb1 O9 77.58(10) . . ?
O2 Tb1 O9 76.41(11) 2_665 . ?
O1 Tb1 O9 141.84(11) 1_565 . ?
O5 Tb1 O9 73.31(10) 2_676 . ?
O7 Tb1 O9 129.28(10) 2_565 . ?
O8 Tb1 O9 141.50(10) . . ?
O1 N1 C5 119.1(4) . . ?
O1 N1 C6 119.5(4) . . ?
C5 N1 C6 121.4(4) . . ?
O4 N2 C11 119.6(4) . . ?
O4 N2 C12 118.8(4) . . ?
C11 N2 C12 121.6(4) . . ?
O3 C1 O2 124.8(4) . . ?
O3 C1 C2 117.9(4) . . ?
O2 C1 C2 117.3(4) . . ?
C6 C2 C3 119.3(4) . . ?
C6 C2 C1 120.1(4) . . ?
C3 C2 C1 120.6(4) . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 120.3(5) . . ?
N1 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
N1 C6 C2 120.2(4) . . ?
N1 C6 H6 119.9 . . ?
C2 C6 H6 119.9 . . ?
O6 C7 O5 126.7(4) . . ?
O6 C7 C8 117.0(4) . . ?
O5 C7 C8 116.3(4) . . ?
C12 C8 C9 119.6(4) . . ?
C12 C8 C7 118.7(4) . . ?
C9 C8 C7 121.6(4) . . ?
C10 C9 C8 118.2(4) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N2 C11 C10 119.7(4) . . ?
N2 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
N2 C12 C8 120.1(4) . . ?
N2 C12 H12 119.9 . . ?
C8 C12 H12 119.9 . . ?
O8 C13 O7 126.7(4) . . ?
O8 C13 C13 117.1(4) . 2_565 ?
O7 C13 C13 116.3(4) . 2_565 ?
N1 O1 Tb1 132.5(2) . 1_545 ?
C1 O2 Tb1 126.3(3) . 2_665 ?
C1 O3 Tb1 175.9(3) . . ?
N2 O4 Tb1 124.3(2) . . ?
C7 O5 Tb1 133.3(3) . 2_676 ?
C13 O7 Tb1 118.3(3) . 2_565 ?
C13 O8 Tb1 117.2(3) . . ?
Tb1 O9 H9A 112.1 . . ?
Tb1 O9 H9B 109.5 . . ?
H9A O9 H9B 109.3 . . ?

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
O3 C1 C2 C6 173.9(4) . . . . ?
O2 C1 C2 C6 -6.6(6) . . . . ?
O3 C1 C2 C3 -7.7(6) . . . . ?
O2 C1 C2 C3 171.8(4) . . . . ?
C6 C2 C3 C4 1.9(6) . . . . ?
C1 C2 C3 C4 -176.5(4) . . . . ?
C2 C3 C4 C5 -3.0(6) . . . . ?
O1 N1 C5 C4 -179.2(4) . . . . ?
C6 N1 C5 C4 0.6(7) . . . . ?
C3 C4 C5 N1 1.7(7) . . . . ?
O1 N1 C6 C2 178.1(3) . . . . ?
C5 N1 C6 C2 -1.7(6) . . . . ?
C3 C2 C6 N1 0.4(6) . . . . ?
C1 C2 C6 N1 178.8(4) . . . . ?
O6 C7 C8 C12 150.0(4) . . . . ?
O5 C7 C8 C12 -31.8(6) . . . . ?
O6 C7 C8 C9 -32.7(6) . . . . ?
O5 C7 C8 C9 145.6(4) . . . . ?
C12 C8 C9 C10 0.7(6) . . . . ?
C7 C8 C9 C10 -176.7(4) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
O4 N2 C11 C10 178.8(4) . . . . ?
C12 N2 C11 C10 1.5(6) . . . . ?
C9 C10 C11 N2 -1.2(6) . . . . ?
O4 N2 C12 C8 -178.1(4) . . . . ?
C11 N2 C12 C8 -0.7(6) . . . . ?
C9 C8 C12 N2 -0.4(6) . . . . ?
C7 C8 C12 N2 177.0(4) . . . . ?
C5 N1 O1 Tb1 -97.6(4) . . . 1_545 ?
C6 N1 O1 Tb1 82.6(5) . . . 1_545 ?
O3 C1 O2 Tb1 -12.6(6) . . . 2_665 ?
C2 C1 O2 Tb1 167.9(3) . . . 2_665 ?
O2 C1 O3 Tb1 134(4) . . . . ?
C2 C1 O3 Tb1 -46(4) . . . . ?
O4 Tb1 O3 C1 87(4) . . . . ?
O2 Tb1 O3 C1 -125(4) 2_665 . . . ?
O1 Tb1 O3 C1 -34(4) 1_565 . . . ?
O5 Tb1 O3 C1 149(4) 2_676 . . . ?
O7 Tb1 O3 C1 -51(4) 2_565 . . . ?
O8 Tb1 O3 C1 17(4) . . . . ?
O9 Tb1 O3 C1 166(4) . . . . ?
C11 N2 O4 Tb1 123.0(3) . . . . ?
C12 N2 O4 Tb1 -59.6(4) . . . . ?
O3 Tb1 O4 N2 -135.4(3) . . . . ?
O2 Tb1 O4 N2 113.6(3) 2_665 . . . ?
O1 Tb1 O4 N2 10.9(3) 1_565 . . . ?
O5 Tb1 O4 N2 76.9(3) 2_676 . . . ?
O7 Tb1 O4 N2 -75.0(3) 2_565 . . . ?
O8 Tb1 O4 N2 -48.5(3) . . . . ?
O9 Tb1 O4 N2 152.2(3) . . . . ?
O6 C7 O5 Tb1 28.2(7) . . . 2_676 ?
C8 C7 O5 Tb1 -149.9(3) . . . 2_676 ?
O8 C13 O7 Tb1 -165.0(3) . . . 2_565 ?
C13 C13 O7 Tb1 13.6(6) 2_565 . . 2_565 ?
O7 C13 O8 Tb1 -166.2(3) . . . . ?
C13 C13 O8 Tb1 15.3(6) 2_565 . . . ?
O3 Tb1 O8 C13 -88.9(3) . . . . ?
O4 Tb1 O8 C13 -175.1(3) . . . . ?
O2 Tb1 O8 C13 20.4(4) 2_665 . . . ?
O1 Tb1 O8 C13 61.6(3) 1_565 . . . ?
O5 Tb1 O8 C13 121.2(3) 2_676 . . . ?
O7 Tb1 O8 C13 -15.8(3) 2_565 . . . ?
O9 Tb1 O8 C13 -141.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.886
_refine_diff_density_min         -1.579
_refine_diff_density_rms         0.176
