# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_sm
_database_code_depnum_ccdc_archive 'CCDC 1553879'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 N3 O7 Sm'
_chemical_formula_sum            'C11 H8 N3 O7 Sm'
_chemical_formula_weight         444.55

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'
Sm Sm -0.1638 3.4418 '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 1 21/c 1'

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

_cell_length_a                   6.8473(14)
_cell_length_b                   10.0614(19)
_cell_length_c                   18.471(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.454(2)
_cell_angle_gamma                90.00
_cell_volume                     1270.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2338
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.06

_exptl_crystal_description       block
_exptl_crystal_colour            yellowblock
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             852
_exptl_absorpt_coefficient_mu    4.666
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4100
_diffrn_reflns_av_R_equivalents  0.0127
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         25.10
_reflns_number_total             2202
_reflns_number_gt                1921
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0167P)²+2.6440P] 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         2202
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0194
_refine_ls_wR_factor_ref         0.0449
_refine_ls_wR_factor_gt          0.0431
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.10785(2) 0.997004(16) 0.374516(8) 0.00895(7) Uani 1 1 d . . .
O3 O -0.0518(3) 0.8733(2) 0.26882(12) 0.0173(5) Uani 1 1 d . . .
O1 O -0.0647(4) 0.8069(2) 0.41611(13) 0.0197(5) Uani 1 1 d . . .
C3 C -0.1897(5) 0.6375(3) 0.48863(19) 0.0156(7) Uani 1 1 d . . .
N3 N 0.3182(4) 0.8283(3) 0.31334(15) 0.0164(6) Uani 1 1 d . . .
C6 C -0.1168(4) 0.7772(3) 0.47767(18) 0.0119(7) Uani 1 1 d . . .
N1 N -0.3033(5) 0.3757(3) 0.5113(2) 0.0363(9) Uani 1 1 d . . .
C4 C -0.2008(5) 0.5475(4) 0.4316(2) 0.0229(8) Uani 1 1 d . . .
H4 H -0.1706 0.5729 0.3852 0.028 Uiso 1 1 calc R . .
C2 C -0.2400(5) 0.5942(4) 0.5565(2) 0.0258(9) Uani 1 1 d . . .
H2 H -0.2381 0.6523 0.5957 0.031 Uiso 1 1 calc R . .
C1 C -0.2928(6) 0.4628(4) 0.5644(3) 0.0365(11) Uani 1 1 d . . .
H1 H -0.3228 0.4341 0.6103 0.044 Uiso 1 1 calc R . .
C5 C -0.2582(6) 0.4186(4) 0.4459(3) 0.0356(10) Uani 1 1 d . . .
H5 H -0.2658 0.3583 0.4077 0.043 Uiso 1 1 calc R . .
N2 N 0.5506(4) 0.7255(3) 0.25965(15) 0.0177(6) Uani 1 1 d . . .
H2A H 0.6660 0.6999 0.2500 0.021 Uiso 1 1 calc R . .
C9 C 0.5080(5) 0.8063(4) 0.31393(19) 0.0189(8) Uani 1 1 d . . .
H9 H 0.5999 0.8421 0.3476 0.023 Uiso 1 1 calc R . .
C10 C 0.3794(5) 0.6903(3) 0.22191(18) 0.0142(7) Uani 1 1 d . . .
C8 C 0.2354(5) 0.7554(3) 0.25660(17) 0.0130(7) Uani 1 1 d . . .
O4 O -0.0783(3) 0.6818(3) 0.20885(13) 0.0201(6) Uani 1 1 d . . .
C7 C 0.0206(4) 0.7708(3) 0.24313(16) 0.0119(7) Uani 1 1 d . . .
O1W O 0.3248(4) 0.8959(2) 0.47023(13) 0.0203(5) Uani 1 1 d . . .
H1WA H 0.3173 0.9398 0.5099 0.030 Uiso 1 1 d R . .
H1WB H 0.4438 0.8973 0.4578 0.030 Uiso 1 1 d R . .
O5 O 0.2336(3) 0.5679(2) 0.12354(12) 0.0162(5) Uani 1 1 d . . .
O6 O 0.5588(3) 0.5899(2) 0.13455(13) 0.0189(5) Uani 1 1 d . . .
C11 C 0.3898(5) 0.6083(3) 0.15516(17) 0.0122(7) Uani 1 1 d . . .
O2 O -0.1101(4) 0.8534(3) 0.53117(14) 0.0244(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm1 O2 2.302(3) 3_576 ?
Sm1 O1 2.399(2) . ?
Sm1 O4 2.415(2) 2 ?
Sm1 O5 2.447(2) 2 ?
Sm1 O1W 2.460(2) . ?
Sm1 O6 2.482(2) 2_655 ?
Sm1 O3 2.510(2) . ?
Sm1 N3 2.536(3) . ?
O3 C7 1.250(4) . ?
O1 C6 1.248(4) . ?
C3 C4 1.388(5) . ?
C3 C2 1.390(5) . ?
C3 C6 1.509(5) . ?
N3 C9 1.317(4) . ?
N3 C8 1.374(4) . ?
C6 O2 1.249(4) . ?
N1 C1 1.314(6) . ?
N1 C5 1.337(6) . ?
C4 C5 1.385(6) . ?
C2 C1 1.380(6) . ?
N2 C9 1.336(4) . ?
N2 C10 1.374(4) . ?
C10 C8 1.374(5) . ?
C10 C11 1.489(5) . ?
C8 C7 1.485(4) . ?
O4 C7 1.268(4) . ?
O4 Sm1 2.415(2) 2_545 ?
O5 C11 1.255(4) . ?
O5 Sm1 2.447(2) 2_545 ?
O6 C11 1.253(4) . ?
O6 Sm1 2.482(2) 2_645 ?
O2 Sm1 2.302(3) 3_576 ?

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 Sm1 O1 105.07(9) 3_576 . ?
O2 Sm1 O4 88.60(9) 3_576 2 ?
O1 Sm1 O4 142.58(8) . 2 ?
O2 Sm1 O5 76.17(8) 3_576 2 ?
O1 Sm1 O5 74.83(8) . 2 ?
O4 Sm1 O5 75.01(7) 2 2 ?
O2 Sm1 O1W 75.53(9) 3_576 . ?
O1 Sm1 O1W 74.20(8) . . ?
O4 Sm1 O1W 143.18(8) 2 . ?
O5 Sm1 O1W 130.25(8) 2 . ?
O2 Sm1 O6 80.83(9) 3_576 2_655 ?
O1 Sm1 O6 142.63(8) . 2_655 ?
O4 Sm1 O6 73.09(8) 2 2_655 ?
O5 Sm1 O6 140.79(8) 2 2_655 ?
O1W Sm1 O6 71.71(8) . 2_655 ?
O2 Sm1 O3 153.62(8) 3_576 . ?
O1 Sm1 O3 69.75(8) . . ?
O4 Sm1 O3 82.53(8) 2 . ?
O5 Sm1 O3 77.54(8) 2 . ?
O1W Sm1 O3 124.74(8) . . ?
O6 Sm1 O3 119.58(8) 2_655 . ?
O2 Sm1 N3 142.85(9) 3_576 . ?
O1 Sm1 N3 85.00(9) . . ?
O4 Sm1 N3 105.03(9) 2 . ?
O5 Sm1 N3 140.42(8) 2 . ?
O1W Sm1 N3 73.07(9) . . ?
O6 Sm1 N3 70.88(9) 2_655 . ?
O3 Sm1 N3 63.50(8) . . ?
C7 O3 Sm1 122.72(19) . . ?
C6 O1 Sm1 131.0(2) . . ?
C4 C3 C2 118.3(3) . . ?
C4 C3 C6 120.6(3) . . ?
C2 C3 C6 121.0(3) . . ?
C9 N3 C8 106.1(3) . . ?
C9 N3 Sm1 134.1(2) . . ?
C8 N3 Sm1 118.6(2) . . ?
O1 C6 O2 125.1(3) . . ?
O1 C6 C3 117.4(3) . . ?
O2 C6 C3 117.5(3) . . ?
C1 N1 C5 117.0(4) . . ?
C5 C4 C3 118.0(4) . . ?
C1 C2 C3 118.5(4) . . ?
N1 C1 C2 124.2(4) . . ?
N1 C5 C4 124.0(4) . . ?
C9 N2 C10 108.6(3) . . ?
N3 C9 N2 110.9(3) . . ?
N2 C10 C8 104.8(3) . . ?
N2 C10 C11 118.8(3) . . ?
C8 C10 C11 136.2(3) . . ?
N3 C8 C10 109.6(3) . . ?
N3 C8 C7 115.6(3) . . ?
C10 C8 C7 134.7(3) . . ?
C7 O4 Sm1 152.1(2) . 2_545 ?
O3 C7 O4 124.1(3) . . ?
O3 C7 C8 115.7(3) . . ?
O4 C7 C8 120.2(3) . . ?
C11 O5 Sm1 151.1(2) . 2_545 ?
C11 O6 Sm1 161.1(2) . 2_645 ?
O6 C11 O5 125.9(3) . . ?
O6 C11 C10 115.1(3) . . ?
O5 C11 C10 118.9(3) . . ?
C6 O2 Sm1 176.6(2) . 3_576 ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.099
####################################################################### 
# 
# 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 1551506'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H8 Eu N3 O7'
_chemical_formula_sum            'C11 H8 Eu N3 O7'
_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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   6.8351(6)
_cell_length_b                   10.0382(9)
_cell_length_c                   18.4454(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5310(10)
_cell_angle_gamma                90.00
_cell_volume                     1263.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2026
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            darkyellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    5.009
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3594
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2195
_reflns_number_gt                1837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0218P)²+1.8962P] 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         2195
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0508
_refine_ls_wR_factor_gt          0.0475
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.10787(2) 1.003020(18) 0.374303(8) 0.00862(8) Uani 1 1 d . . .
O5 O 0.1091(4) 0.8543(3) 0.46817(15) 0.0226(7) Uani 1 1 d . . .
C7 C 0.1899(5) 0.6383(4) 0.5113(2) 0.0151(8) Uani 1 1 d . . .
C6 C 0.1163(5) 0.7780(4) 0.5219(2) 0.0126(8) Uani 1 1 d . . .
C8 C 0.2400(6) 0.5953(5) 0.4431(2) 0.0251(10) Uani 1 1 d . . .
H8 H 0.2378 0.6536 0.4038 0.030 Uiso 1 1 calc R . .
N3 N 0.3041(5) 0.3754(4) 0.4888(3) 0.0356(10) Uani 1 1 d . . .
C9 C 0.2934(7) 0.4627(5) 0.4354(3) 0.0354(12) Uani 1 1 d . . .
H9 H 0.3236 0.4336 0.3895 0.042 Uiso 1 1 calc R . .
C10 C 0.2586(7) 0.4187(5) 0.5541(3) 0.0351(12) Uani 1 1 d . . .
H10 H 0.2664 0.3586 0.5925 0.042 Uiso 1 1 calc R . .
C11 C 0.2003(6) 0.5485(4) 0.5680(2) 0.0222(9) Uani 1 1 d . . .
H11 H 0.1691 0.5741 0.6144 0.027 Uiso 1 1 calc R . .
O1 O -0.0533(4) 1.1266(3) 0.26882(14) 0.0168(6) Uani 1 1 d . . .
N1 N 0.3166(4) 1.1709(3) 0.31366(17) 0.0165(7) Uani 1 1 d . . .
C1 C 0.0198(5) 1.2298(4) 0.24299(19) 0.0123(8) Uani 1 1 d . . .
C2 C 0.2345(5) 1.2449(4) 0.2568(2) 0.0129(8) Uani 1 1 d . . .
N2 N 0.5494(4) 1.2753(3) 0.26046(18) 0.0173(7) Uani 1 1 d . . .
H2 H 0.6650 1.3015 0.2511 0.021 Uiso 1 1 calc R . .
C3 C 0.3784(5) 1.3108(4) 0.2222(2) 0.0131(8) Uani 1 1 d . . .
O2 O -0.0795(4) 1.3187(3) 0.20886(14) 0.0185(6) Uani 1 1 d . . .
C5 C 0.5073(5) 1.1939(4) 0.3144(2) 0.0179(9) Uani 1 1 d . . .
H5 H 0.5997 1.1580 0.3480 0.022 Uiso 1 1 calc R . .
O3 O 0.2325(3) 1.4327(3) 0.12370(14) 0.0151(6) Uani 1 1 d . . .
C4 C 0.3900(5) 1.3915(4) 0.15551(19) 0.0115(8) Uani 1 1 d . . .
O4 O 0.5588(3) 1.4099(3) 0.13456(14) 0.0170(6) Uani 1 1 d . . .
O6 O 0.0635(4) 0.8079(3) 0.58342(14) 0.0192(6) Uani 1 1 d . . .
O1W O 0.3270(4) 1.1023(3) 0.46972(14) 0.0186(6) Uani 1 1 d . . .
H1WA H 0.3036 1.0688 0.5106 0.028 Uiso 1 1 d R . .
H1WB H 0.3074 1.1859 0.4707 0.028 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
Eu1 O5 2.286(3) . ?
Eu1 O6 2.386(3) 3_576 ?
Eu1 O2 2.404(3) 2_545 ?
Eu1 O3 2.434(2) 2_545 ?
Eu1 O1W 2.452(3) . ?
Eu1 O4 2.478(2) 2_645 ?
Eu1 O1 2.505(3) . ?
Eu1 N1 2.514(3) . ?
O5 C6 1.251(5) . ?
C7 C11 1.380(6) . ?
C7 C8 1.393(6) . ?
C7 C6 1.506(5) . ?
C6 O6 1.249(5) . ?
C8 C9 1.390(7) . ?
N3 C9 1.318(7) . ?
N3 C10 1.334(7) . ?
C10 C11 1.391(6) . ?
O1 C1 1.257(4) . ?
N1 C5 1.323(5) . ?
N1 C2 1.377(5) . ?
C1 O2 1.265(4) . ?
C1 C2 1.482(5) . ?
C2 C3 1.374(5) . ?
N2 C5 1.332(5) . ?
N2 C3 1.374(5) . ?
C3 C4 1.479(5) . ?
O2 Eu1 2.404(3) 2 ?
O3 C4 1.263(4) . ?
O3 Eu1 2.434(2) 2 ?
C4 O4 1.253(4) . ?
O4 Eu1 2.477(2) 2_655 ?
O6 Eu1 2.386(3) 3_576 ?

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
O5 Eu1 O6 104.53(10) . 3_576 ?
O5 Eu1 O2 88.68(11) . 2_545 ?
O6 Eu1 O2 143.02(9) 3_576 2_545 ?
O5 Eu1 O3 76.00(9) . 2_545 ?
O6 Eu1 O3 74.73(9) 3_576 2_545 ?
O2 Eu1 O3 75.34(8) 2_545 2_545 ?
O5 Eu1 O1W 75.42(10) . . ?
O6 Eu1 O1W 74.48(9) 3_576 . ?
O2 Eu1 O1W 142.46(9) 2_545 . ?
O3 Eu1 O1W 130.50(9) 2_545 . ?
O5 Eu1 O4 80.98(9) . 2_645 ?
O6 Eu1 O4 142.52(9) 3_576 2_645 ?
O2 Eu1 O4 72.90(9) 2_545 2_645 ?
O3 Eu1 O4 140.86(9) 2_545 2_645 ?
O1W Eu1 O4 71.16(9) . 2_645 ?
O5 Eu1 O1 153.22(9) . . ?
O6 Eu1 O1 70.05(9) 3_576 . ?
O2 Eu1 O1 82.60(9) 2_545 . ?
O3 Eu1 O1 77.31(9) 2_545 . ?
O1W Eu1 O1 125.19(9) . . ?
O4 Eu1 O1 119.85(9) 2_645 . ?
O5 Eu1 N1 143.03(10) . . ?
O6 Eu1 N1 85.18(10) 3_576 . ?
O2 Eu1 N1 104.93(10) 2_545 . ?
O3 Eu1 N1 140.38(9) 2_545 . ?
O1W Eu1 N1 73.05(10) . . ?
O4 Eu1 N1 70.97(10) 2_645 . ?
O1 Eu1 N1 63.71(9) . . ?
C6 O5 Eu1 176.4(3) . . ?
C11 C7 C8 118.7(4) . . ?
C11 C7 C6 120.7(4) . . ?
C8 C7 C6 120.5(4) . . ?
O6 C6 O5 124.9(4) . . ?
O6 C6 C7 117.4(3) . . ?
O5 C6 C7 117.7(3) . . ?
C9 C8 C7 118.0(4) . . ?
C9 N3 C10 117.0(4) . . ?
N3 C9 C8 124.3(5) . . ?
N3 C10 C11 123.9(5) . . ?
C7 C11 C10 118.2(4) . . ?
C1 O1 Eu1 122.5(2) . . ?
C5 N1 C2 105.5(3) . . ?
C5 N1 Eu1 134.3(3) . . ?
C2 N1 Eu1 119.0(2) . . ?
O1 C1 O2 123.8(3) . . ?
O1 C1 C2 115.6(3) . . ?
O2 C1 C2 120.6(3) . . ?
C3 C2 N1 110.1(3) . . ?
C3 C2 C1 134.4(3) . . ?
N1 C2 C1 115.4(3) . . ?
C5 N2 C3 109.0(3) . . ?
N2 C3 C2 104.3(3) . . ?
N2 C3 C4 118.8(3) . . ?
C2 C3 C4 136.5(3) . . ?
C1 O2 Eu1 151.7(2) . 2 ?
N1 C5 N2 111.0(3) . . ?
C4 O3 Eu1 151.1(2) . 2 ?
O4 C4 O3 125.6(3) . . ?
O4 C4 C3 115.8(3) . . ?
O3 C4 C3 118.5(3) . . ?
C4 O4 Eu1 160.8(3) . 2_655 ?
C6 O6 Eu1 131.6(3) . 3_576 ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.138
####################################################################### 
# 
# 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_Gd
_database_code_depnum_ccdc_archive 'CCDC 1553878'
_audit_update_record             
;
2017-06-02 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 N3 Nd O7'
_chemical_formula_weight         438.44

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'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   6.8672(12)
_cell_length_b                   10.1098(18)
_cell_length_c                   18.617(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.655(4)
_cell_angle_gamma                90.00
_cell_volume                     1289.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3892
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.02

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    4.068
_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      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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6009
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2253
_reflns_number_gt                2079
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0195P)²+2.0007P] 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         2253
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_ref         0.0491
_refine_ls_wR_factor_gt          0.0478
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.10808(2) -0.002668(13) 0.375004(7) 0.00910(7) Uani 1 1 d . . .
O4 O -0.0498(3) -0.1276(2) 0.26898(11) 0.0181(4) Uani 1 1 d . . .
O6 O 0.1113(3) 0.1475(2) 0.47028(12) 0.0260(5) Uani 1 1 d . . .
C7 C 0.1903(4) 0.3633(3) 0.51191(16) 0.0166(6) Uani 1 1 d . . .
N2 N 0.3208(3) -0.1716(2) 0.31291(13) 0.0176(5) Uani 1 1 d . . .
C6 C 0.1191(4) 0.2245(3) 0.52313(15) 0.0139(6) Uani 1 1 d . . .
C3 C 0.2371(4) -0.2441(3) 0.25589(15) 0.0133(6) Uani 1 1 d . . .
N3 N 0.3032(4) 0.6234(3) 0.4889(2) 0.0394(8) Uani 1 1 d . . .
C8 C 0.2389(5) 0.4061(3) 0.44415(18) 0.0274(7) Uani 1 1 d . . .
H8 H 0.2359 0.3479 0.4054 0.033 Uiso 1 1 calc R . .
C10 C 0.2596(5) 0.5807(3) 0.5540(2) 0.0379(9) Uani 1 1 d . . .
H10 H 0.2678 0.6407 0.5919 0.046 Uiso 1 1 calc R . .
C4 C 0.0231(4) -0.2288(3) 0.24324(14) 0.0129(6) Uani 1 1 d . . .
C11 C 0.2030(5) 0.4525(3) 0.56815(19) 0.0263(7) Uani 1 1 d . . .
H11 H 0.1743 0.4270 0.6143 0.032 Uiso 1 1 calc R . .
C9 C 0.2915(5) 0.5368(4) 0.4359(2) 0.0390(10) Uani 1 1 d . . .
H9 H 0.3204 0.5654 0.3903 0.047 Uiso 1 1 calc R . .
O1W O 0.3275(3) -0.1043(2) 0.47128(11) 0.0209(5) Uani 1 1 d . . .
H1WA H 0.4471 -0.0873 0.4639 0.031 Uiso 1 1 d R . .
H1WB H 0.3111 -0.1886 0.4712 0.031 Uiso 1 1 d R . .
O3 O -0.0759(3) -0.3175(2) 0.20893(11) 0.0206(5) Uani 1 1 d . . .
C5 C 0.5097(4) -0.1930(3) 0.31264(16) 0.0206(6) Uani 1 1 d . . .
H5 H 0.6021 -0.1570 0.3457 0.025 Uiso 1 1 calc R . .
N1 N 0.5518(3) -0.2732(3) 0.25853(13) 0.0186(5) Uani 1 1 d . . .
H1 H 0.6667 -0.2984 0.2487 0.022 Uiso 1 1 calc R . .
C2 C 0.3805(4) -0.3083(3) 0.22135(15) 0.0145(6) Uani 1 1 d . . .
O2 O 0.2351(3) -0.4302(2) 0.12355(10) 0.0173(4) Uani 1 1 d . . .
O1 O 0.5583(3) -0.4089(2) 0.13440(11) 0.0195(4) Uani 1 1 d . . .
C1 C 0.3906(4) -0.3898(3) 0.15500(14) 0.0124(6) Uani 1 1 d . . .
O5 O 0.0664(3) 0.1955(2) 0.58431(11) 0.0215(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O6 2.334(2) . ?
Nd1 O5 2.435(2) 3_556 ?
Nd1 O3 2.439(2) 2 ?
Nd1 O2 2.4697(19) 2 ?
Nd1 O1W 2.489(2) . ?
Nd1 O1 2.4956(19) 2_655 ?
Nd1 O4 2.529(2) . ?
Nd1 N2 2.570(2) . ?
O4 C4 1.248(3) . ?
O6 C6 1.253(4) . ?
C7 C11 1.380(5) . ?
C7 C8 1.394(4) . ?
C7 C6 1.505(4) . ?
N2 C5 1.316(4) . ?
N2 C3 1.384(4) . ?
C6 O5 1.251(3) . ?
C3 C2 1.373(4) . ?
C3 C4 1.481(4) . ?
N3 C9 1.317(6) . ?
N3 C10 1.338(5) . ?
C8 C9 1.382(5) . ?
C10 C11 1.383(5) . ?
C4 O3 1.272(3) . ?
O3 Nd1 2.439(2) 2_545 ?
C5 N1 1.339(4) . ?
N1 C2 1.373(4) . ?
C2 C1 1.490(4) . ?
O2 C1 1.253(3) . ?
O2 Nd1 2.4697(19) 2_545 ?
O1 C1 1.252(3) . ?
O1 Nd1 2.4956(19) 2_645 ?
O5 Nd1 2.435(2) 3_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Nd1 O5 105.40(7) . 3_556 ?
O6 Nd1 O3 89.07(8) . 2 ?
O5 Nd1 O3 141.96(7) 3_556 2 ?
O6 Nd1 O2 76.20(7) . 2 ?
O5 Nd1 O2 75.24(7) 3_556 2 ?
O3 Nd1 O2 74.45(6) 2 2 ?
O6 Nd1 O1W 75.25(8) . . ?
O5 Nd1 O1W 74.49(7) 3_556 . ?
O3 Nd1 O1W 143.53(7) 2 . ?
O2 Nd1 O1W 130.46(7) 2 . ?
O6 Nd1 O1 80.90(7) . 2_655 ?
O5 Nd1 O1 142.97(7) 3_556 2_655 ?
O3 Nd1 O1 73.11(7) 2 2_655 ?
O2 Nd1 O1 140.25(7) 2 2_655 ?
O1W Nd1 O1 72.02(7) . 2_655 ?
O6 Nd1 O4 154.29(7) . . ?
O5 Nd1 O4 69.37(7) 3_556 . ?
O3 Nd1 O4 82.33(7) 2 . ?
O2 Nd1 O4 78.16(6) 2 . ?
O1W Nd1 O4 124.44(7) . . ?
O1 Nd1 O4 119.01(7) 2_655 . ?
O6 Nd1 N2 142.77(8) . . ?
O5 Nd1 N2 84.99(7) 3_556 . ?
O3 Nd1 N2 104.64(8) 2 . ?
O2 Nd1 N2 140.56(7) 2 . ?
O1W Nd1 N2 73.39(7) . . ?
O1 Nd1 N2 70.76(7) 2_655 . ?
O4 Nd1 N2 62.90(7) . . ?
C4 O4 Nd1 123.14(17) . . ?
C6 O6 Nd1 177.1(2) . . ?
C11 C7 C8 118.5(3) . . ?
C11 C7 C6 120.6(3) . . ?
C8 C7 C6 120.9(3) . . ?
C5 N2 C3 105.8(2) . . ?
C5 N2 Nd1 134.41(19) . . ?
C3 N2 Nd1 118.46(18) . . ?
O5 C6 O6 124.7(3) . . ?
O5 C6 C7 117.4(3) . . ?
O6 C6 C7 117.9(3) . . ?
C2 C3 N2 109.5(2) . . ?
C2 C3 C4 135.1(3) . . ?
N2 C3 C4 115.2(2) . . ?
C9 N3 C10 117.2(3) . . ?
C9 C8 C7 118.4(3) . . ?
N3 C10 C11 123.8(3) . . ?
O4 C4 O3 123.8(2) . . ?
O4 C4 C3 116.3(2) . . ?
O3 C4 C3 120.0(2) . . ?
C7 C11 C10 118.2(3) . . ?
N3 C9 C8 123.8(4) . . ?
C4 O3 Nd1 152.37(18) . 2_545 ?
N2 C5 N1 111.2(2) . . ?
C5 N1 C2 108.5(2) . . ?
N1 C2 C3 105.0(2) . . ?
N1 C2 C1 118.5(2) . . ?
C3 C2 C1 136.2(3) . . ?
C1 O2 Nd1 151.28(18) . 2_545 ?
C1 O1 Nd1 161.17(19) . 2_645 ?
O1 C1 O2 125.5(3) . . ?
O1 C1 C2 115.6(2) . . ?
O2 C1 C2 119.0(2) . . ?
C6 O5 Nd1 130.30(18) . 3_556 ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.108
