# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_eu
_database_code_depnum_ccdc_archive 'CCDC 1004349'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 Eu N3 O6'
_chemical_formula_sum            'C8 H8 Eu N3 O6'
_chemical_formula_weight         394.13

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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'

_cell_length_a                   10.173(2)
_cell_length_b                   10.372(2)
_cell_length_c                   11.119(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1173.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    5.370
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11459
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2689
_reflns_number_gt                2642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_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)+(0.0158P)²+1.1118P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.016(13)
_refine_ls_number_reflns         2689
_refine_ls_number_parameters     167
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0156
_refine_ls_R_factor_gt           0.0149
_refine_ls_wR_factor_ref         0.0342
_refine_ls_wR_factor_gt          0.0340
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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
Eu Eu 0.142107(14) 0.613151(14) 0.146032(11) 0.01296(4) Uani 1 1 d . . .
O1 O 0.1773(2) 0.4856(2) -0.0351(2) 0.0295(6) Uani 1 1 d . . .
O2 O 0.3134(3) 0.3709(3) -0.1505(2) 0.0387(6) Uani 1 1 d . . .
O3 O 0.1387(3) 0.8400(2) 0.1797(2) 0.0403(6) Uani 1 1 d . . .
O4 O -0.0151(2) 0.9288(2) 0.2959(2) 0.0304(6) Uani 1 1 d . . .
O5 O -0.0095(3) 1.1879(3) 0.5111(2) 0.0383(7) Uani 1 1 d . . .
O6 O 0.1615(2) 1.3011(2) 0.5723(2) 0.0309(6) Uani 1 1 d . . .
N1 N 0.3180(3) 0.4341(3) 0.1610(2) 0.0248(6) Uani 1 1 d . . .
N2 N 0.4015(3) 0.3879(4) 0.2422(2) 0.0363(7) Uani 1 1 d D . .
H2 H 0.407(5) 0.431(4) 0.315(3) 0.053(14) Uiso 1 1 d D . .
N3 N 0.0966(3) 1.1623(3) 0.2857(2) 0.0231(6) Uani 1 1 d . . .
H3 H 0.0947 1.2389 0.2457 0.028 Uiso 1 1 calc R . .
C1 C 0.4835(5) 0.2990(6) 0.1947(4) 0.0544(15) Uani 1 1 d . . .
H1 H 0.5490 0.2538 0.2351 0.065 Uiso 1 1 calc R . .
C2 C 0.4518(5) 0.2882(5) 0.0757(4) 0.0471(12) Uani 1 1 d . . .
H2A H 0.4913 0.2357 0.0184 0.056 Uiso 1 1 calc R . .
C3 C 0.3483(4) 0.3724(3) 0.0591(3) 0.0303(7) Uani 1 1 d . . .
C4 C 0.2750(3) 0.4120(3) -0.0501(3) 0.0246(7) Uani 1 1 d . . .
C5 C 0.0859(4) 0.9345(3) 0.2295(3) 0.0260(7) Uani 1 1 d . . .
C6 C 0.1451(4) 1.0657(3) 0.2016(4) 0.0350(8) Uani 1 1 d . . .
H6A H 0.2401 1.0608 0.2070 0.042 Uiso 1 1 calc R . .
H6B H 0.1222 1.0907 0.1202 0.042 Uiso 1 1 calc R . .
C7 C 0.1799(4) 1.1803(5) 0.3914(4) 0.0486(12) Uani 1 1 d . . .
H7A H 0.2491 1.2412 0.3720 0.058 Uiso 1 1 calc R . .
H7B H 0.2210 1.0988 0.4116 0.058 Uiso 1 1 calc R . .
C8 C 0.1047(3) 1.2290(3) 0.4993(3) 0.0237(7) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Eu 0.01358(6) 0.01419(6) 0.01112(6) 0.00205(6) 0.00201(6) 0.00216(5)
O1 0.0331(15) 0.0358(13) 0.0195(11) -0.0062(10) -0.0037(9) 0.0115(10)
O2 0.0552(15) 0.0458(16) 0.0151(10) -0.0020(13) 0.0044(10) 0.0191(11)
O3 0.0461(15) 0.0211(11) 0.0537(16) -0.0077(11) 0.0203(14) 0.0034(12)
O4 0.0293(13) 0.0180(12) 0.0439(15) -0.0044(11) 0.0128(11) -0.0002(9)
O5 0.0329(15) 0.059(2) 0.0227(12) -0.0069(12) -0.0006(10) -0.0247(13)
O6 0.0249(14) 0.0336(13) 0.0341(13) -0.0066(11) -0.0131(10) -0.0075(10)
N1 0.0241(14) 0.0303(14) 0.0198(13) 0.0039(12) -0.0004(10) 0.0085(10)
N2 0.0410(18) 0.0526(19) 0.0152(12) 0.0059(16) -0.0003(11) 0.0142(17)
N3 0.0247(14) 0.0168(12) 0.0278(14) -0.0063(11) 0.0059(10) -0.0030(10)
C1 0.050(3) 0.083(4) 0.031(2) 0.008(2) -0.0046(19) 0.039(3)
C2 0.056(3) 0.059(3) 0.027(2) -0.0005(19) 0.0028(18) 0.036(2)
C3 0.0349(19) 0.0323(19) 0.0236(14) 0.0018(16) 0.0026(16) 0.0086(19)
C4 0.0330(18) 0.0219(18) 0.0189(14) 0.0019(13) 0.0017(13) 0.0049(13)
C5 0.0280(17) 0.0224(16) 0.0278(16) -0.0061(14) 0.0020(14) 0.0023(14)
C6 0.0303(18) 0.0282(17) 0.046(2) -0.0078(16) 0.0175(18) -0.0033(17)
C7 0.023(2) 0.075(3) 0.049(2) -0.022(2) -0.0018(15) -0.0077(19)
C8 0.0207(16) 0.0244(18) 0.0260(15) 0.0003(14) -0.0072(11) -0.0054(12)

_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
Eu O2 2.313(2) 2_565 ?
Eu O6 2.336(2) 2_574 ?
Eu O5 2.339(2) 4_545 ?
Eu O3 2.383(2) . ?
Eu O4 2.397(2) 4_545 ?
Eu O1 2.436(2) . ?
Eu N1 2.585(3) . ?
Eu N3 2.595(3) 4_545 ?
Eu C8 3.218(3) 4_545 ?
O1 C4 1.264(4) . ?
O2 C4 1.257(4) . ?
O2 Eu 2.313(2) 2_564 ?
O3 C5 1.247(4) . ?
O4 C5 1.267(4) . ?
O4 Eu 2.397(2) 4 ?
O5 C8 1.245(4) . ?
O5 Eu 2.339(2) 4 ?
O6 C8 1.246(4) . ?
O6 Eu 2.336(2) 2_575 ?
N1 N2 1.328(4) . ?
N1 C3 1.338(4) . ?
N2 C1 1.351(6) . ?
N3 C6 1.456(4) . ?
N3 C7 1.461(5) . ?
N3 Eu 2.595(3) 4 ?
C1 C2 1.366(6) . ?
C2 C3 1.380(5) . ?
C3 C4 1.483(5) . ?
C5 C6 1.520(5) . ?
C7 C8 1.510(5) . ?
C8 Eu 3.218(3) 4 ?

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 Eu O6 98.55(10) 2_565 2_574 ?
O2 Eu O5 145.04(9) 2_565 4_545 ?
O6 Eu O5 96.02(10) 2_574 4_545 ?
O2 Eu O3 77.20(9) 2_565 . ?
O6 Eu O3 72.04(9) 2_574 . ?
O5 Eu O3 77.40(11) 4_545 . ?
O2 Eu O4 84.22(10) 2_565 4_545 ?
O6 Eu O4 149.26(8) 2_574 4_545 ?
O5 Eu O4 98.90(10) 4_545 4_545 ?
O3 Eu O4 137.55(9) . 4_545 ?
O2 Eu O1 144.95(8) 2_565 . ?
O6 Eu O1 77.91(9) 2_574 . ?
O5 Eu O1 69.35(9) 4_545 . ?
O3 Eu O1 131.93(9) . . ?
O4 Eu O1 82.46(9) 4_545 . ?
O2 Eu N1 81.53(9) 2_565 . ?
O6 Eu N1 72.78(9) 2_574 . ?
O5 Eu N1 133.29(9) 4_545 . ?
O3 Eu N1 135.19(10) . . ?
O4 Eu N1 77.43(9) 4_545 . ?
O1 Eu N1 63.99(8) . . ?
O2 Eu N3 83.28(9) 2_565 4_545 ?
O6 Eu N3 145.95(9) 2_574 4_545 ?
O5 Eu N3 67.28(9) 4_545 4_545 ?
O3 Eu N3 75.31(9) . 4_545 ?
O4 Eu N3 64.75(9) 4_545 4_545 ?
O1 Eu N3 119.09(8) . 4_545 ?
N1 Eu N3 140.38(9) . 4_545 ?
O2 Eu C8 128.10(9) 2_565 4_545 ?
O6 Eu C8 110.42(9) 2_574 4_545 ?
O5 Eu C8 18.47(9) 4_545 4_545 ?
O3 Eu C8 72.48(10) . 4_545 ?
O4 Eu C8 90.72(9) 4_545 4_545 ?
O1 Eu C8 84.40(8) . 4_545 ?
N1 Eu C8 147.23(9) . 4_545 ?
N3 Eu C8 48.97(9) 4_545 4_545 ?
C4 O1 Eu 123.5(2) . . ?
C4 O2 Eu 154.8(2) . 2_564 ?
C5 O3 Eu 148.4(2) . . ?
C5 O4 Eu 123.8(2) . 4 ?
C8 O5 Eu 125.0(2) . 4 ?
C8 O6 Eu 148.6(2) . 2_575 ?
N2 N1 C3 104.9(3) . . ?
N2 N1 Eu 138.2(2) . . ?
C3 N1 Eu 116.6(2) . . ?
N1 N2 C1 112.0(3) . . ?
C6 N3 C7 114.1(3) . . ?
C6 N3 Eu 111.7(2) . 4 ?
C7 N3 Eu 109.4(2) . 4 ?
N2 C1 C2 106.7(4) . . ?
C1 C2 C3 105.0(4) . . ?
N1 C3 C2 111.4(3) . . ?
N1 C3 C4 116.5(3) . . ?
C2 C3 C4 132.0(3) . . ?
O2 C4 O1 124.5(3) . . ?
O2 C4 C3 118.5(3) . . ?
O1 C4 C3 117.1(3) . . ?
O3 C5 O4 124.8(3) . . ?
O3 C5 C6 116.2(3) . . ?
O4 C5 C6 118.8(3) . . ?
N3 C6 C5 110.6(3) . . ?
N3 C7 C8 112.9(3) . . ?
O5 C8 O6 124.7(3) . . ?
O5 C8 C7 116.2(3) . . ?
O6 C8 C7 118.9(3) . . ?
O5 C8 Eu 36.55(16) . 4 ?
O6 C8 Eu 155.9(3) . 4 ?
C7 C8 Eu 82.6(2) . 4 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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_sm
_database_code_depnum_ccdc_archive 'CCDC 1004350'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 N3 O6 Sm'
_chemical_formula_sum            'C8 H8 N3 O6 Sm'
_chemical_formula_weight         392.52

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'
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'
Sm Sm -0.1638 3.4418 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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'

_cell_length_a                   10.243(2)
_cell_length_b                   10.371(2)
_cell_length_c                   11.131(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1182.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    4.989
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11631
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2709
_reflns_number_gt                2691
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_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)+(0.0079P)²+0.8142P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(11)
_refine_ls_number_reflns         2709
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0131
_refine_ls_R_factor_gt           0.0129
_refine_ls_wR_factor_ref         0.0290
_refine_ls_wR_factor_gt          0.0289
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_chemical_absolute_configuration ad

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
Sm Sm 0.142761(11) 0.614510(11) 0.353732(10) 0.01175(3) Uani 1 1 d . . .
O2 O 0.3121(2) 0.3691(2) 0.64940(18) 0.0362(5) Uani 1 1 d . . .
O4 O -0.1382(2) 0.34252(18) 0.1786(2) 0.0371(5) Uani 1 1 d . . .
N2 N 0.4003(2) 0.3863(3) 0.2577(2) 0.0308(5) Uani 1 1 d . . .
N1 N 0.3176(2) 0.4334(2) 0.3381(2) 0.0213(5) Uani 1 1 d . . .
O1 O 0.17824(19) 0.48602(19) 0.53543(17) 0.0257(4) Uani 1 1 d . . .
C3 C 0.3459(3) 0.3722(3) 0.4406(3) 0.0268(6) Uani 1 1 d . . .
C4 C 0.2737(3) 0.4114(2) 0.5499(2) 0.0210(5) Uani 1 1 d . . .
C2 C 0.4486(4) 0.2860(4) 0.4241(3) 0.0421(9) Uani 1 1 d . . .
H2A H 0.4868 0.2325 0.4812 0.051 Uiso 1 1 calc R . .
O3 O 0.0150(2) 0.43066(19) 0.2941(2) 0.0297(5) Uani 1 1 d . . .
C1 C 0.4810(4) 0.2972(4) 0.3058(3) 0.0481(11) Uani 1 1 d . . .
H1 H 0.5463 0.2521 0.2657 0.058 Uiso 1 1 calc R . .
C6 C -0.0848(3) 0.4366(3) 0.2281(3) 0.0234(6) Uani 1 1 d . . .
C5 C -0.1435(3) 0.5683(3) 0.2012(3) 0.0335(7) Uani 1 1 d . . .
H5A H -0.1205 0.5939 0.1201 0.040 Uiso 1 1 calc R . .
H5B H -0.2379 0.5631 0.2061 0.040 Uiso 1 1 calc R . .
O5 O 0.0099(2) 0.6879(2) 0.51158(19) 0.0348(5) Uani 1 1 d . . .
C8 C -0.1044(3) 0.7283(3) 0.4999(3) 0.0219(6) Uani 1 1 d . . .
O6 O -0.16058(19) 0.79981(19) 0.57319(19) 0.0289(4) Uani 1 1 d . . .
C7 C -0.1782(3) 0.6804(4) 0.3923(3) 0.0460(10) Uani 1 1 d . . .
H7A H -0.2178 0.5980 0.4116 0.055 Uiso 1 1 calc R . .
H7B H -0.2479 0.7406 0.3739 0.055 Uiso 1 1 calc R . .
N3 N -0.0959(2) 0.6650(2) 0.2863(2) 0.0225(5) Uani 1 1 d . . .
H3 H -0.0945 0.7421 0.2474 0.027 Uiso 1 1 calc R . .
H2 H 0.407(4) 0.420(4) 0.188(4) 0.046(11) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sm 0.01154(5) 0.01370(5) 0.01002(5) -0.00218(5) -0.00198(5) 0.00233(5)
O2 0.0509(11) 0.0438(12) 0.0141(8) 0.0022(11) -0.0018(9) 0.0218(9)
O4 0.0426(11) 0.0188(9) 0.0500(14) -0.0072(9) -0.0189(11) -0.0037(10)
N2 0.0368(13) 0.0447(14) 0.0108(10) -0.0032(12) -0.0001(9) 0.0120(13)
N1 0.0211(10) 0.0283(11) 0.0143(11) -0.0042(9) -0.0003(8) 0.0084(8)
O1 0.0298(11) 0.0304(10) 0.0170(9) 0.0041(8) 0.0049(7) 0.0120(8)
C3 0.0289(13) 0.0288(14) 0.0228(12) -0.0008(12) -0.0029(13) 0.0082(15)
C4 0.0268(12) 0.0195(13) 0.0167(12) -0.0022(10) -0.0023(10) 0.0036(10)
C2 0.051(2) 0.053(2) 0.0230(16) -0.0012(15) -0.0045(15) 0.0349(18)
O3 0.0272(10) 0.0182(9) 0.0436(13) -0.0047(9) -0.0141(9) 0.0025(8)
C1 0.044(2) 0.070(3) 0.0301(18) -0.0068(18) 0.0018(15) 0.035(2)
C6 0.0262(13) 0.0204(12) 0.0236(14) -0.0035(11) -0.0030(12) -0.0017(11)
C5 0.0299(14) 0.0252(13) 0.0453(17) -0.0081(12) -0.0188(15) 0.0049(14)
O5 0.0295(11) 0.0565(15) 0.0185(10) -0.0065(10) 0.0004(8) 0.0241(11)
C8 0.0192(12) 0.0218(14) 0.0248(13) 0.0015(11) 0.0052(10) 0.0041(10)
O6 0.0228(10) 0.0321(10) 0.0317(11) -0.0052(8) 0.0128(9) 0.0060(9)
C7 0.0208(14) 0.071(3) 0.046(2) -0.0211(18) 0.0002(13) 0.0072(15)
N3 0.0230(11) 0.0161(10) 0.0286(13) -0.0053(9) -0.0066(9) 0.0024(9)

_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
Sm O2 2.327(2) 2_564 ?
Sm O6 2.3472(18) 3_566 ?
Sm O5 2.349(2) . ?
Sm O4 2.392(2) 4 ?
Sm O3 2.406(2) . ?
Sm O1 2.4492(19) . ?
Sm N1 2.601(2) . ?
Sm N3 2.610(2) . ?
O2 C4 1.254(3) . ?
O2 Sm 2.327(2) 2_565 ?
O4 C6 1.247(3) . ?
O4 Sm 2.392(2) 4_545 ?
N2 N1 1.326(3) . ?
N2 C1 1.350(4) . ?
N1 C3 1.337(3) . ?
O1 C4 1.257(3) . ?
C3 C2 1.393(4) . ?
C3 C4 1.481(4) . ?
C2 C1 1.363(5) . ?
O3 C6 1.260(3) . ?
C6 C5 1.522(4) . ?
C5 N3 1.464(4) . ?
O5 C8 1.250(3) . ?
C8 O6 1.244(3) . ?
C8 C7 1.501(4) . ?
O6 Sm 2.3472(18) 3_466 ?
C7 N3 1.458(4) . ?

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 Sm O6 98.08(8) 2_564 3_566 ?
O2 Sm O5 145.34(7) 2_564 . ?
O6 Sm O5 96.62(8) 3_566 . ?
O2 Sm O4 77.57(8) 2_564 4 ?
O6 Sm O4 72.24(7) 3_566 4 ?
O5 Sm O4 77.35(9) . 4 ?
O2 Sm O3 84.05(8) 2_564 . ?
O6 Sm O3 149.60(7) 3_566 . ?
O5 Sm O3 98.50(8) . . ?
O4 Sm O3 136.97(7) 4 . ?
O2 Sm O1 144.81(6) 2_564 . ?
O6 Sm O1 78.02(7) 3_566 . ?
O5 Sm O1 69.18(7) . . ?
O4 Sm O1 131.69(7) 4 . ?
O3 Sm O1 82.95(7) . . ?
O2 Sm N1 81.40(7) 2_564 . ?
O6 Sm N1 72.89(7) 3_566 . ?
O5 Sm N1 133.06(8) . . ?
O4 Sm N1 135.84(8) 4 . ?
O3 Sm N1 77.51(7) . . ?
O1 Sm N1 63.90(7) . . ?
O2 Sm N3 83.72(8) 2_564 . ?
O6 Sm N3 145.83(7) 3_566 . ?
O5 Sm N3 66.88(7) . . ?
O4 Sm N3 74.92(8) 4 . ?
O3 Sm N3 64.55(7) . . ?
O1 Sm N3 119.05(7) . . ?
N1 Sm N3 140.40(7) . . ?
C4 O2 Sm 154.14(18) . 2_565 ?
C6 O4 Sm 148.09(19) . 4_545 ?
N1 N2 C1 112.1(3) . . ?
N2 N1 C3 105.2(2) . . ?
N2 N1 Sm 138.68(19) . . ?
C3 N1 Sm 115.80(17) . . ?
C4 O1 Sm 123.79(17) . . ?
N1 C3 C2 110.9(3) . . ?
N1 C3 C4 117.5(2) . . ?
C2 C3 C4 131.5(3) . . ?
O2 C4 O1 124.9(2) . . ?
O2 C4 C3 118.2(2) . . ?
O1 C4 C3 116.9(2) . . ?
C1 C2 C3 104.8(3) . . ?
C6 O3 Sm 124.27(18) . . ?
N2 C1 C2 107.0(3) . . ?
O4 C6 O3 125.1(3) . . ?
O4 C6 C5 116.2(2) . . ?
O3 C6 C5 118.6(2) . . ?
N3 C5 C6 110.8(2) . . ?
C8 O5 Sm 124.97(19) . . ?
O6 C8 O5 124.4(3) . . ?
O6 C8 C7 119.2(3) . . ?
O5 C8 C7 116.3(3) . . ?
C8 O6 Sm 148.2(2) . 3_466 ?
N3 C7 C8 113.0(2) . . ?
C7 N3 C5 113.9(3) . . ?
C7 N3 Sm 109.33(18) . . ?
C5 N3 Sm 111.13(17) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.069
