# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_gt-2-eu
_database_code_depnum_ccdc_archive 'CCDC 1012765'
_audit_update_record             
;
2014-07-08 deposited with the CCDC.
2016-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 Eu O9, C2 H8 N, 3(H2 O)'
_chemical_formula_sum            'C6 H16 Eu N O12'
_chemical_formula_weight         446.16

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n   '
_symmetry_space_group_name_Hall  '-P 2yn   '

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                   9.6706(10)
_cell_length_b                   11.7551(13)
_cell_length_c                   12.3115(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.2690(10)
_cell_angle_gamma                90.00
_cell_volume                     1381.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1485
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.79

_exptl_crystal_description       'Block '
_exptl_crystal_colour            'Colorless '
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    4.601
_exptl_absorpt_correction_type   'multi-scan '
_exptl_absorpt_correction_T_min  0.5652
_exptl_absorpt_correction_T_max  0.6562
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex2 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9869
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2565
_reflns_number_gt                1980
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0201P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2565
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0584
_refine_ls_wR_factor_gt          0.0543
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_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
Eu1 Eu 0.28617(2) 1.015537(13) 0.169091(15) 0.01788(5) Uani 1 1 d . . .
O1 O 0.3605(3) 1.2154(2) 0.1563(2) 0.0292(8) Uani 1 1 d . . .
O1W O 0.4545(3) 1.0231(2) 0.3460(2) 0.0334(7) Uani 1 1 d . . .
H1WA H 0.4811 0.9611 0.3781 0.050 Uiso 1 1 d R . .
H1WB H 0.4066 1.0591 0.3870 0.050 Uiso 1 1 d R . .
O2 O 0.1921(3) 1.14080(18) 0.2943(2) 0.0243(7) Uani 1 1 d . . .
O2W O 0.4189(4) 1.1575(2) 0.5347(3) 0.0598(11) Uani 1 1 d . . .
H2WA H 0.4490 1.2144 0.5028 0.090 Uiso 1 1 d R . .
H2WB H 0.3412 1.1764 0.5534 0.090 Uiso 1 1 d R . .
O3W O 0.1725(4) 0.9928(3) 0.5083(3) 0.0738(12) Uani 1 1 d . . .
H3WA H 0.1616 1.0639 0.5160 0.111 Uiso 1 1 d R . .
H3WB H 0.1267 0.9803 0.4445 0.111 Uiso 1 1 d R . .
O3 O 0.3160(3) 1.39480(19) 0.2001(2) 0.0283(7) Uani 1 1 d . . .
O4 O 0.1339(3) 1.31971(19) 0.3278(2) 0.0218(7) Uani 1 1 d . . .
O4W O -0.0822(4) 0.7824(3) 0.4687(3) 0.0782(13) Uani 1 1 d . . .
H4WA H -0.0414 0.7344 0.4330 0.117 Uiso 1 1 d R . .
H4WB H -0.1172 0.7462 0.5175 0.117 Uiso 1 1 d R . .
O5 O 0.3186(2) 1.0118(2) -0.0227(2) 0.0288(7) Uani 1 1 d . . .
O6 O 0.4664(3) 0.9863(2) -0.14230(19) 0.0245(7) Uani 1 1 d . . .
O7 O 0.1023(3) 0.8911(2) 0.0671(2) 0.0323(8) Uani 1 1 d . . .
O8 O -0.0839(3) 0.8819(2) -0.0666(2) 0.0290(8) Uani 1 1 d . . .
C1 C 0.3012(4) 1.2890(3) 0.2061(3) 0.0225(10) Uani 1 1 d . . .
C2 C 0.1998(4) 1.2452(3) 0.2822(3) 0.0171(9) Uani 1 1 d . . .
C3 C 0.4379(4) 0.9990(3) -0.0469(3) 0.0226(10) Uani 1 1 d . . .
C4 C 0.0059(4) 0.9341(3) 0.0008(3) 0.0230(9) Uani 1 1 d . . .
C5 C 0.6933(6) 1.2451(4) 0.3332(5) 0.082(2) Uani 1 1 d . . .
H5A H 0.6141 1.2417 0.3711 0.124 Uiso 1 1 calc R . .
H5B H 0.6698 1.2898 0.2675 0.124 Uiso 1 1 calc R . .
H5C H 0.7711 1.2793 0.3801 0.124 Uiso 1 1 calc R . .
C6 C 0.8506(5) 1.1227(5) 0.2447(4) 0.080(2) Uani 1 1 d . . .
H6A H 0.8680 1.0443 0.2295 0.119 Uiso 1 1 calc R . .
H6B H 0.9321 1.1547 0.2890 0.119 Uiso 1 1 calc R . .
H6C H 0.8301 1.1640 0.1767 0.119 Uiso 1 1 calc R . .
N1 N 0.7311(4) 1.1304(3) 0.3039(3) 0.0435(12) Uani 1 1 d . . .
H1A H 0.6563 1.0985 0.2621 0.052 Uiso 1 1 calc R . .
H1B H 0.7506 1.0890 0.3660 0.052 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 2.413(2) . ?
Eu1 O4 2.427(2) 2_545 ?
Eu1 O5 2.432(2) . ?
Eu1 O8 2.466(2) 3_575 ?
Eu1 O6 2.467(2) 3_675 ?
Eu1 O3 2.469(3) 2_545 ?
Eu1 O1 2.470(2) . ?
Eu1 O7 2.482(3) . ?
Eu1 O1W 2.502(2) . ?
Eu1 C2 3.209(3) . ?
Eu1 C2 3.233(3) 2_545 ?
Eu1 C3 3.244(4) . ?
Eu1 H1WB 2.7941 . ?
O1 C1 1.251(4) . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8501 . ?
O2 C2 1.240(4) . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8500 . ?
O3 C1 1.255(4) . ?
O3 Eu1 2.469(3) 2 ?
O4 C2 1.267(4) . ?
O4 Eu1 2.427(2) 2 ?
O4W H4WA 0.8499 . ?
O4W H4WB 0.8500 . ?
O5 C3 1.246(4) . ?
O6 C3 1.257(4) . ?
O6 Eu1 2.467(2) 3_675 ?
O7 C4 1.243(4) . ?
O8 C4 1.259(4) . ?
O8 Eu1 2.465(2) 3_575 ?
C1 C2 1.550(5) . ?
C1 Eu1 3.253(4) 2 ?
C2 Eu1 3.233(3) 2 ?
C3 C3 1.527(7) 3_675 ?
C4 C4 1.554(7) 3_575 ?
C5 N1 1.457(6) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 N1 1.465(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?

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 O4 136.12(8) . 2_545 ?
O2 Eu1 O5 138.77(8) . . ?
O4 Eu1 O5 84.69(8) 2_545 . ?
O2 Eu1 O8 71.28(8) . 3_575 ?
O4 Eu1 O8 134.14(8) 2_545 3_575 ?
O5 Eu1 O8 74.19(9) . 3_575 ?
O2 Eu1 O6 124.35(8) . 3_675 ?
O4 Eu1 O6 71.35(8) 2_545 3_675 ?
O5 Eu1 O6 65.83(8) . 3_675 ?
O8 Eu1 O6 129.97(8) 3_575 3_675 ?
O2 Eu1 O3 72.69(8) . 2_545 ?
O4 Eu1 O3 66.71(8) 2_545 2_545 ?
O5 Eu1 O3 138.65(8) . 2_545 ?
O8 Eu1 O3 104.30(9) 3_575 2_545 ?
O6 Eu1 O3 125.50(8) 3_675 2_545 ?
O2 Eu1 O1 66.66(8) . . ?
O4 Eu1 O1 143.92(9) 2_545 . ?
O5 Eu1 O1 82.58(9) . . ?
O8 Eu1 O1 73.57(8) 3_575 . ?
O6 Eu1 O1 72.63(8) 3_675 . ?
O3 Eu1 O1 137.70(8) 2_545 . ?
O2 Eu1 O7 111.71(9) . . ?
O4 Eu1 O7 69.47(8) 2_545 . ?
O5 Eu1 O7 72.06(9) . . ?
O8 Eu1 O7 65.44(8) 3_575 . ?
O6 Eu1 O7 123.93(8) 3_675 . ?
O3 Eu1 O7 70.24(9) 2_545 . ?
O1 Eu1 O7 136.11(8) . . ?
O2 Eu1 O1W 71.42(8) . . ?
O4 Eu1 O1W 81.91(8) 2_545 . ?
O5 Eu1 O1W 132.71(8) . . ?
O8 Eu1 O1W 141.22(8) 3_575 . ?
O6 Eu1 O1W 66.91(8) 3_675 . ?
O3 Eu1 O1W 74.07(8) 2_545 . ?
O1 Eu1 O1W 82.31(8) . . ?
O7 Eu1 O1W 140.74(8) . . ?
O2 Eu1 C2 19.66(8) . . ?
O4 Eu1 C2 153.60(9) 2_545 . ?
O5 Eu1 C2 121.32(9) . . ?
O8 Eu1 C2 64.55(8) 3_575 . ?
O6 Eu1 C2 113.03(8) 3_675 . ?
O3 Eu1 C2 92.35(8) 2_545 . ?
O1 Eu1 C2 47.63(9) . . ?
O7 Eu1 C2 120.00(9) . . ?
O1W Eu1 C2 76.73(8) . . ?
O2 Eu1 C2 119.35(9) . 2_545 ?
O4 Eu1 C2 20.09(9) 2_545 2_545 ?
O5 Eu1 C2 98.87(9) . 2_545 ?
O8 Eu1 C2 125.58(8) 3_575 2_545 ?
O6 Eu1 C2 90.20(8) 3_675 2_545 ?
O3 Eu1 C2 47.42(9) 2_545 2_545 ?
O1 Eu1 C2 160.59(9) . 2_545 ?
O7 Eu1 C2 61.30(8) . 2_545 ?
O1W Eu1 C2 82.63(8) . 2_545 ?
C2 Eu1 C2 138.81(3) . 2_545 ?
O2 Eu1 C3 145.81(8) . . ?
O4 Eu1 C3 76.75(8) 2_545 . ?
O5 Eu1 C3 19.39(8) . . ?
O8 Eu1 C3 92.06(9) 3_575 . ?
O6 Eu1 C3 46.63(8) 3_675 . ?
O3 Eu1 C3 141.43(8) 2_545 . ?
O1 Eu1 C3 80.21(9) . . ?
O7 Eu1 C3 86.08(9) . . ?
O1W Eu1 C3 113.52(9) . . ?
C2 Eu1 C3 126.15(9) . . ?
C2 Eu1 C3 94.71(9) 2_545 . ?
O2 Eu1 H1WB 54.3 . . ?
O4 Eu1 H1WB 94.4 2_545 . ?
O5 Eu1 H1WB 146.8 . . ?
O8 Eu1 H1WB 125.1 3_575 . ?
O6 Eu1 H1WB 82.3 3_675 . ?
O3 Eu1 H1WB 68.2 2_545 . ?
O1 Eu1 H1WB 78.8 . . ?
O7 Eu1 H1WB 138.4 . . ?
O1W Eu1 H1WB 17.4 . . ?
C2 Eu1 H1WB 61.7 . . ?
C2 Eu1 H1WB 90.2 2_545 . ?
C3 Eu1 H1WB 128.6 . . ?
C1 O1 Eu1 117.7(2) . . ?
Eu1 O1W H1WA 118.7 . . ?
Eu1 O1W H1WB 101.2 . . ?
H1WA O1W H1WB 107.7 . . ?
C2 O2 Eu1 119.4(2) . . ?
H2WA O2W H2WB 107.7 . . ?
H3WA O3W H3WB 102.6 . . ?
C1 O3 Eu1 118.0(2) . 2 ?
C2 O4 Eu1 118.8(2) . 2 ?
H4WA O4W H4WB 107.7 . . ?
C3 O5 Eu1 120.2(2) . . ?
C3 O6 Eu1 119.3(2) . 3_675 ?
C4 O7 Eu1 119.6(2) . . ?
C4 O8 Eu1 120.3(2) . 3_575 ?
O1 C1 O3 126.2(4) . . ?
O1 C1 C2 116.8(3) . . ?
O3 C1 C2 117.0(3) . . ?
O1 C1 Eu1 42.31(17) . . ?
O3 C1 Eu1 167.3(3) . . ?
C2 C1 Eu1 74.76(18) . . ?
O1 C1 Eu1 166.3(3) . 2 ?
O3 C1 Eu1 42.08(18) . 2 ?
C2 C1 Eu1 75.45(18) . 2 ?
Eu1 C1 Eu1 150.17(13) . 2 ?
O2 C2 O4 125.9(3) . . ?
O2 C2 C1 117.3(3) . . ?
O4 C2 C1 116.8(3) . . ?
O2 C2 Eu1 40.93(17) . . ?
O4 C2 Eu1 163.5(2) . . ?
C1 C2 Eu1 77.47(18) . . ?
O2 C2 Eu1 162.2(3) . 2 ?
O4 C2 Eu1 41.15(16) . 2 ?
C1 C2 Eu1 76.90(18) . 2 ?
Eu1 C2 Eu1 154.32(13) . 2 ?
O5 C3 O6 126.0(3) . . ?
O5 C3 C3 117.6(4) . 3_675 ?
O6 C3 C3 116.4(4) . 3_675 ?
O5 C3 Eu1 40.38(17) . . ?
O6 C3 Eu1 165.7(2) . . ?
C3 C3 Eu1 77.5(3) 3_675 . ?
O7 C4 O8 126.8(3) . . ?
O7 C4 C4 117.3(4) . 3_575 ?
O8 C4 C4 115.8(4) . 3_575 ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 N1 C6 115.4(4) . . ?
C5 N1 H1A 108.4 . . ?
C6 N1 H1A 108.4 . . ?
C5 N1 H1B 108.4 . . ?
C6 N1 H1B 108.4 . . ?
H1A N1 H1B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.150

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