# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_j
_audit_block_doi                 10.5517/cc13jd67
_database_code_depnum_ccdc_archive 'CCDC 1028648'
_audit_update_record             
;
2014-10-11 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 N8 O18 Tb2'
_chemical_formula_weight         960.33

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           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9698(4)
_cell_length_b                   9.7137(5)
_cell_length_c                   10.3770(5)
_cell_angle_alpha                116.8630(10)
_cell_angle_beta                 107.2860(10)
_cell_angle_gamma                95.6960(10)
_cell_volume                     658.07(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    5.435
_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  ?
_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            4848
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         28.31
_reflns_number_total             3238
_reflns_number_gt                3063
_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)+(0.0253P)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         3238
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.003
_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
C7 C 0.1479(4) 0.5469(4) -0.1701(4) 0.0134(6) Uani 1 1 d . . .
Tb1 Tb 0.207600(19) 0.203611(17) 0.303901(16) 0.01208(7) Uani 1 1 d . . .
O1 O 0.1352(3) 0.2122(3) 0.0762(3) 0.0179(5) Uani 1 1 d . . .
O2 O -0.1261(3) 0.0810(3) -0.1321(3) 0.0166(5) Uani 1 1 d . . .
O3 O -0.2236(3) 0.2754(3) -0.5291(3) 0.0194(5) Uani 1 1 d . . .
O4 O -0.1620(4) 0.5432(3) -0.4029(3) 0.0205(5) Uani 1 1 d . . .
O7 O 0.4825(4) 0.2747(4) 0.2631(4) 0.0225(6) Uani 1 1 d . . .
O6 O -0.1196(4) 0.1279(3) 0.1785(3) 0.0191(5) Uani 1 1 d . . .
O9 O 0.4271(4) 0.0752(4) 0.3967(4) 0.0256(6) Uani 1 1 d . . .
O8 O 0.4325(4) 0.3762(4) 0.5671(3) 0.0232(6) Uani 1 1 d . . .
N5 N 0.5260(4) 0.7273(4) 0.2195(3) 0.0179(6) Uani 1 1 d . . .
N6 N 0.6674(4) 0.8545(4) 0.2770(4) 0.0192(6) Uani 1 1 d . . .
N7 N 0.6551(4) 0.8933(4) 0.1698(4) 0.0189(6) Uani 1 1 d . . .
N8 N 0.5074(4) 0.7914(4) 0.0379(3) 0.0175(6) Uani 1 1 d . . .
O5 O 0.0772(5) 0.1305(4) 0.4505(4) 0.0234(6) Uani 1 1 d . . .
C9 C 0.0217(4) 0.1938(4) -0.0468(4) 0.0124(6) Uani 1 1 d . . .
C4 C 0.0647(4) 0.3143(4) -0.0942(4) 0.0121(6) Uani 1 1 d . . .
C3 C 0.2205(4) 0.4417(4) 0.0041(4) 0.0140(6) Uani 1 1 d . . .
C6 C -0.0102(4) 0.4199(4) -0.2679(4) 0.0133(6) Uani 1 1 d . . .
C8 C -0.1406(4) 0.4133(4) -0.4103(4) 0.0132(6) Uani 1 1 d . . .
C1 C 0.4316(4) 0.6911(4) 0.0735(4) 0.0142(6) Uani 1 1 d . . .
C2 C 0.2666(4) 0.5569(4) -0.0336(4) 0.0136(6) Uani 1 1 d . . .
C5 C -0.0501(5) 0.3009(4) -0.2324(4) 0.0143(6) Uani 1 1 d . . .
H3 H -0.176(6) 0.061(6) 0.183(5) 0.012(10) Uiso 1 1 d . . .
H4 H -0.149(6) 0.117(6) 0.107(6) 0.021(14) Uiso 1 1 d . . .
H6 H 0.571(8) 0.273(6) 0.313(7) 0.033(15) Uiso 1 1 d . . .
H5 H 0.482(6) 0.244(6) 0.185(6) 0.018(12) Uiso 1 1 d . . .
H7 H 0.433(9) 0.458(8) 0.607(8) 0.050(19) Uiso 1 1 d . . .
H2 H -0.011(8) 0.152(7) 0.466(6) 0.031(14) Uiso 1 1 d . . .
H8 H 0.458(8) 0.358(8) 0.647(8) 0.057(18) Uiso 1 1 d . . .
H1 H 0.135(8) 0.126(7) 0.504(7) 0.030(17) Uiso 1 1 d . . .
H11 H -0.159(5) 0.218(5) -0.298(4) 0.005(8) Uiso 1 1 d . . .
H12 H 0.175(5) 0.629(5) -0.195(4) 0.006(8) Uiso 1 1 d . . .
H13 H 0.297(6) 0.443(5) 0.089(5) 0.015(10) Uiso 1 1 d . . .
H9 H 0.527(11) 0.115(10) 0.437(9) 0.09(3) Uiso 1 1 d . . .
H10 H 0.407(8) -0.025(9) 0.323(8) 0.062(19) 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
C7 C6 1.392(5) . ?
C7 C2 1.405(5) . ?
C7 H12 0.97(4) . ?
Tb1 O1 2.303(2) . ?
Tb1 O4 2.314(3) 2_565 ?
Tb1 O5 2.381(3) . ?
Tb1 O2 2.396(2) 2 ?
Tb1 O6 2.402(3) . ?
Tb1 O8 2.416(3) . ?
Tb1 O7 2.443(3) . ?
Tb1 O9 2.462(3) . ?
O1 C9 1.247(4) . ?
O2 C9 1.273(4) . ?
O2 Tb1 2.396(2) 2 ?
O3 C8 1.264(4) . ?
O4 C8 1.261(4) . ?
O4 Tb1 2.314(3) 2_565 ?
O7 H6 0.75(6) . ?
O7 H5 0.73(5) . ?
O6 H3 0.78(5) . ?
O6 H4 0.67(5) . ?
O9 H9 0.75(8) . ?
O9 H10 0.88(7) . ?
O8 H7 0.71(7) . ?
O8 H8 0.90(7) . ?
N5 C1 1.331(4) . ?
N5 N6 1.346(4) . ?
N6 N7 1.308(4) . ?
N7 N8 1.351(4) . ?
N8 C1 1.338(4) . ?
O5 H2 0.79(6) . ?
O5 H1 0.63(6) . ?
C9 C4 1.507(4) . ?
C4 C3 1.384(5) . ?
C4 C5 1.391(5) . ?
C3 C2 1.392(5) . ?
C3 H13 0.90(4) . ?
C6 C5 1.399(5) . ?
C6 C8 1.502(5) . ?
C1 C2 1.465(5) . ?
C5 H11 0.94(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
C6 C7 C2 119.8(3) . . ?
C6 C7 H12 120(2) . . ?
C2 C7 H12 120(2) . . ?
O1 Tb1 O4 83.11(9) . 2_565 ?
O1 Tb1 O5 142.88(10) . . ?
O4 Tb1 O5 94.76(11) 2_565 . ?
O1 Tb1 O2 84.20(9) . 2 ?
O4 Tb1 O2 156.00(9) 2_565 2 ?
O5 Tb1 O2 83.30(10) . 2 ?
O1 Tb1 O6 72.02(10) . . ?
O4 Tb1 O6 81.15(9) 2_565 . ?
O5 Tb1 O6 71.05(11) . . ?
O2 Tb1 O6 75.58(9) 2 . ?
O1 Tb1 O8 133.82(9) . . ?
O4 Tb1 O8 70.84(10) 2_565 . ?
O5 Tb1 O8 78.40(11) . . ?
O2 Tb1 O8 131.39(10) 2 . ?
O6 Tb1 O8 136.26(10) . . ?
O1 Tb1 O7 68.81(10) . . ?
O4 Tb1 O7 96.18(10) 2_565 . ?
O5 Tb1 O7 147.69(12) . . ?
O2 Tb1 O7 98.10(10) 2 . ?
O6 Tb1 O7 140.76(10) . . ?
O8 Tb1 O7 76.70(10) . . ?
O1 Tb1 O9 127.49(10) . . ?
O4 Tb1 O9 136.15(10) 2_565 . ?
O5 Tb1 O9 78.18(11) . . ?
O2 Tb1 O9 67.00(10) 2 . ?
O6 Tb1 O9 133.66(11) . . ?
O8 Tb1 O9 65.33(11) . . ?
O7 Tb1 O9 72.89(10) . . ?
C9 O1 Tb1 151.5(2) . . ?
C9 O2 Tb1 136.1(2) . 2 ?
C8 O4 Tb1 158.8(2) . 2_565 ?
Tb1 O7 H6 118(4) . . ?
Tb1 O7 H5 121(4) . . ?
H6 O7 H5 108(5) . . ?
Tb1 O6 H3 118(3) . . ?
Tb1 O6 H4 114(4) . . ?
H3 O6 H4 112(5) . . ?
Tb1 O9 H9 122(7) . . ?
Tb1 O9 H10 111(4) . . ?
H9 O9 H10 110(7) . . ?
Tb1 O8 H7 118(5) . . ?
Tb1 O8 H8 128(4) . . ?
H7 O8 H8 99(6) . . ?
C1 N5 N6 105.3(3) . . ?
N7 N6 N5 108.9(3) . . ?
N6 N7 N8 110.1(3) . . ?
C1 N8 N7 104.2(3) . . ?
Tb1 O5 H2 125(4) . . ?
Tb1 O5 H1 113(5) . . ?
H2 O5 H1 115(6) . . ?
O1 C9 O2 123.8(3) . . ?
O1 C9 C4 117.0(3) . . ?
O2 C9 C4 119.2(3) . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 C9 118.6(3) . . ?
C5 C4 C9 121.3(3) . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H13 118(3) . . ?
C2 C3 H13 121(3) . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 C8 119.6(3) . . ?
C5 C6 C8 119.9(3) . . ?
O4 C8 O3 124.8(3) . . ?
O4 C8 C6 118.6(3) . . ?
O3 C8 C6 116.7(3) . . ?
N5 C1 N8 111.5(3) . . ?
N5 C1 C2 123.5(3) . . ?
N8 C1 C2 124.9(3) . . ?
C3 C2 C7 119.1(3) . . ?
C3 C2 C1 119.8(3) . . ?
C7 C2 C1 121.0(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H11 121(2) . . ?
C6 C5 H11 119(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.744
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.167
_exptl_crystal_recrystallization_method hydrothermal
_chemical_properties_physical    Photo-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_j
_audit_block_doi                 10.5517/cc13jd78
_database_code_depnum_ccdc_archive 'CCDC 1028649'
_audit_update_record             
;
2014-10-11 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 N4 Nd O9'
_chemical_formula_weight         465.47

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9987(6)
_cell_length_b                   9.8130(6)
_cell_length_c                   10.4856(6)
_cell_angle_alpha                116.667(4)
_cell_angle_beta                 107.471(4)
_cell_angle_gamma                95.656(4)
_cell_volume                     674.77(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             454
_exptl_absorpt_coefficient_mu    3.907
_exptl_absorpt_correction_type   ?
_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            3855
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.14
_reflns_number_total             2403
_reflns_number_gt                2312
_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)+(0.0487P)²+0.5767P] 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         2403
_refine_ls_number_parameters     247
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

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
H9 H -0.024(6) 0.144(10) 0.961(10) 0.08(3) Uiso 1 1 d D . .
H10 H 0.140(9) 0.118(10) 1.030(6) 0.080 Uiso 1 1 d D . .
H1 H 0.554(3) 0.117(7) 0.936(7) 0.052(19) Uiso 1 1 d D . .
H5 H 0.596(4) 0.274(7) 0.813(5) 0.033(14) Uiso 1 1 d D . .
H4 H -0.179(8) 0.113(8) 0.586(4) 0.06(2) Uiso 1 1 d D . .
H2 H 0.426(10) -0.017(3) 0.846(7) 0.07(2) Uiso 1 1 d D . .
H3 H -0.189(9) 0.052(8) 0.668(7) 0.041(17) Uiso 1 1 d . . .
H7 H 0.471(10) 0.354(8) 1.151(8) 0.06(2) Uiso 1 1 d . . .
H8 H 0.425(9) 0.473(4) 1.120(7) 0.06(2) Uiso 1 1 d D . .
H6 H 0.486(6) 0.243(6) 0.664(6) 0.015(11) Uiso 1 1 d . . .
Nd1 Nd 0.20940(2) 0.20478(2) 0.805453(19) 0.01337(10) Uani 1 1 d . . .
O1 O 0.1322(4) 0.2131(3) 0.5739(3) 0.0202(6) Uani 1 1 d . . .
O2 O -0.1270(4) 0.0838(3) 0.3656(3) 0.0201(6) Uani 1 1 d . . .
O3 O -0.1584(4) 0.5382(3) 0.0926(3) 0.0218(6) Uani 1 1 d . . .
O6 O 0.4386(4) 0.3815(4) 1.0749(3) 0.0246(6) Uani 1 1 d D . .
O5 O 0.4908(4) 0.2747(4) 0.7605(4) 0.0247(6) Uani 1 1 d D . .
O7 O 0.4405(4) 0.0802(4) 0.9034(4) 0.0280(7) Uani 1 1 d D . .
O9 O -0.1277(4) 0.1246(4) 0.6746(3) 0.0212(6) Uani 1 1 d D . .
O8 O 0.0757(4) 0.1279(4) 0.9547(4) 0.0258(7) Uani 1 1 d D . .
N4 N 0.5231(5) 0.7243(4) 0.7157(4) 0.0192(7) Uani 1 1 d . . .
N3 N 0.6641(5) 0.8514(4) 0.7725(4) 0.0208(7) Uani 1 1 d . . .
N2 N 0.6516(5) 0.8890(4) 0.6663(4) 0.0208(7) Uani 1 1 d . . .
N1 N 0.5035(5) 0.7883(4) 0.5357(4) 0.0200(7) Uani 1 1 d . . .
C1 C 0.4287(5) 0.6888(4) 0.5712(4) 0.0147(7) Uani 1 1 d . . .
C2 C 0.2633(5) 0.5555(4) 0.4649(4) 0.0148(7) Uani 1 1 d . . .
C7 C 0.1471(5) 0.5456(4) 0.3302(4) 0.0147(7) Uani 1 1 d . . .
H7A H 0.1738 0.6231 0.3058 0.018 Uiso 1 1 calc R . .
C6 C -0.0100(5) 0.4187(4) 0.2319(4) 0.0137(7) Uani 1 1 d . . .
C5 C -0.0505(5) 0.3020(5) 0.2676(4) 0.0161(7) Uani 1 1 d . . .
H5A H -0.1530 0.2159 0.1999 0.019 Uiso 1 1 calc R . .
C4 C 0.0617(5) 0.3139(4) 0.4040(4) 0.0144(7) Uani 1 1 d . . .
C3 C 0.2183(5) 0.4418(4) 0.5030(4) 0.0158(7) Uani 1 1 d . . .
H3A H 0.2931 0.4509 0.5951 0.019 Uiso 1 1 calc R . .
C8 C 0.0200(5) 0.1956(4) 0.4508(4) 0.0138(7) Uani 1 1 d . . .
C9 C -0.1395(5) 0.4098(5) 0.0877(4) 0.0156(7) Uani 1 1 d . . .
O4 O -0.2205(4) 0.2740(3) -0.0289(3) 0.0202(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O1 2.360(3) . ?
Nd1 O3 2.391(3) 2_566 ?
Nd1 O2 2.456(3) 2_556 ?
Nd1 O8 2.463(3) . ?
Nd1 O9 2.482(3) . ?
Nd1 O6 2.494(3) . ?
Nd1 O5 2.527(3) . ?
Nd1 O7 2.529(3) . ?
O1 C8 1.255(5) . ?
O2 C8 1.273(5) . ?
O2 Nd1 2.456(3) 2_556 ?
O3 C9 1.264(5) . ?
O3 Nd1 2.391(3) 2_566 ?
O6 H7 0.92(8) . ?
O6 H8 0.84(2) . ?
O5 H5 0.86(2) . ?
O5 H6 0.90(5) . ?
O7 H1 0.84(2) . ?
O7 H2 0.84(2) . ?
O9 H4 0.84(2) . ?
O9 H3 0.79(6) . ?
O8 H9 0.85(2) . ?
O8 H10 0.86(2) . ?
N4 C1 1.332(5) . ?
N4 N3 1.354(5) . ?
N3 N2 1.303(5) . ?
N2 N1 1.355(5) . ?
N1 C1 1.340(5) . ?
C1 C2 1.473(5) . ?
C2 C7 1.392(6) . ?
C2 C3 1.394(5) . ?
C7 C6 1.398(5) . ?
C7 H7A 0.9300 . ?
C6 C5 1.394(5) . ?
C6 C9 1.513(5) . ?
C5 C4 1.387(6) . ?
C5 H5A 0.9300 . ?
C4 C3 1.401(5) . ?
C4 C8 1.494(5) . ?
C3 H3A 0.9300 . ?
C9 O4 1.258(5) . ?

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
O1 Nd1 O3 83.59(10) . 2_566 ?
O1 Nd1 O2 84.75(10) . 2_556 ?
O3 Nd1 O2 155.89(10) 2_566 2_556 ?
O1 Nd1 O8 142.41(10) . . ?
O3 Nd1 O8 94.24(10) 2_566 . ?
O2 Nd1 O8 82.36(10) 2_556 . ?
O1 Nd1 O9 71.30(10) . . ?
O3 Nd1 O9 81.13(10) 2_566 . ?
O2 Nd1 O9 75.15(10) 2_556 . ?
O8 Nd1 O9 71.29(10) . . ?
O1 Nd1 O6 134.35(10) . . ?
O3 Nd1 O6 70.52(10) 2_566 . ?
O2 Nd1 O6 131.14(10) 2_556 . ?
O8 Nd1 O6 78.20(10) . . ?
O9 Nd1 O6 136.28(10) . . ?
O1 Nd1 O5 68.84(10) . . ?
O3 Nd1 O5 97.60(10) 2_566 . ?
O2 Nd1 O5 97.75(10) 2_556 . ?
O8 Nd1 O5 147.92(10) . . ?
O9 Nd1 O5 139.99(10) . . ?
O6 Nd1 O5 77.87(10) . . ?
O1 Nd1 O7 127.75(11) . . ?
O3 Nd1 O7 135.23(10) 2_566 . ?
O2 Nd1 O7 67.69(10) 2_556 . ?
O8 Nd1 O7 78.62(11) . . ?
O9 Nd1 O7 134.60(10) . . ?
O6 Nd1 O7 64.74(10) . . ?
O5 Nd1 O7 71.98(11) . . ?
C8 O1 Nd1 152.9(3) . . ?
C8 O2 Nd1 136.2(2) . 2_556 ?
C9 O3 Nd1 156.7(3) . 2_566 ?
Nd1 O6 H7 125(4) . . ?
Nd1 O6 H8 115(5) . . ?
H7 O6 H8 105(6) . . ?
Nd1 O5 H5 122(4) . . ?
Nd1 O5 H6 121(3) . . ?
H5 O5 H6 107(5) . . ?
Nd1 O7 H1 124(5) . . ?
Nd1 O7 H2 117(5) . . ?
H1 O7 H2 102(6) . . ?
Nd1 O9 H4 121(5) . . ?
Nd1 O9 H3 122(5) . . ?
H4 O9 H3 101(6) . . ?
Nd1 O8 H9 122(6) . . ?
Nd1 O8 H10 122(5) . . ?
H9 O8 H10 112(8) . . ?
C1 N4 N3 105.1(3) . . ?
N2 N3 N4 109.0(3) . . ?
N3 N2 N1 110.2(3) . . ?
C1 N1 N2 104.1(3) . . ?
N4 C1 N1 111.7(3) . . ?
N4 C1 C2 123.5(3) . . ?
N1 C1 C2 124.8(3) . . ?
C7 C2 C3 119.6(3) . . ?
C7 C2 C1 120.8(3) . . ?
C3 C2 C1 119.6(3) . . ?
C2 C7 C6 119.7(3) . . ?
C2 C7 H7A 120.1 . . ?
C6 C7 H7A 120.1 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 C9 119.7(3) . . ?
C7 C6 C9 119.9(3) . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 C8 122.2(3) . . ?
C3 C4 C8 118.5(3) . . ?
C2 C3 C4 120.8(4) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
O1 C8 O2 123.4(4) . . ?
O1 C8 C4 117.8(3) . . ?
O2 C8 C4 118.8(3) . . ?
O4 C9 O3 124.8(4) . . ?
O4 C9 C6 117.2(3) . . ?
O3 C9 C6 118.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H6 N1 0.90(5) 2.01(5) 2.898(5) 170(4) 2_666
O6 H8 O5 0.84(2) 2.13(3) 2.914(5) 155(6) 2_667
O6 H7 N4 0.92(8) 1.87(8) 2.775(5) 167(6) 2_667
O9 H3 N2 0.79(6) 1.93(7) 2.719(5) 174(6) 1_445
O7 H2 N4 0.84(2) 2.61(4) 3.402(5) 157(7) 1_545
O7 H2 N3 0.84(2) 2.52(6) 3.102(5) 127(6) 1_545
O9 H4 O2 0.84(2) 2.37(4) 3.083(4) 143(6) .
O5 H5 O4 0.86(2) 1.85(3) 2.676(4) 160(5) 1_656
O7 H1 O4 0.84(2) 2.07(4) 2.845(4) 152(6) 1_656
O8 H10 N3 0.86(2) 2.06(3) 2.894(5) 165(8) 2_667
O7 H1 O4 0.84(2) 2.07(4) 2.845(4) 152(6) 1_656
O9 H4 O2 0.84(2) 2.37(4) 3.083(4) 143(6) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.14
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.671
_refine_diff_density_min         -1.481
_refine_diff_density_rms         0.148
_exptl_crystal_recrystallization_method hydrothermal
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_j
_audit_block_doi                 10.5517/cc13jrs5
_database_code_depnum_ccdc_archive 'CCDC 1029007'
_audit_update_record             
;
2014-10-14 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H26 Eu2 N8 O18'
_chemical_formula_weight         946.39

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           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9812(3)
_cell_length_b                   9.7491(4)
_cell_length_c                   10.4153(4)
_cell_angle_alpha                116.8030(10)
_cell_angle_beta                 107.3700(10)
_cell_angle_gamma                95.6700(10)
_cell_volume                     663.93(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'colorloss '
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    4.784
_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  ?
_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            4947
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         28.36
_reflns_number_total             3288
_reflns_number_gt                3105
_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)+(0.0297P)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         3288
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0519
_refine_ls_wR_factor_gt          0.0514
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
H10 H -0.030(7) -0.112(6) 0.065(6) 0.050(16) Uiso 1 1 d . . .
H11 H 0.096(7) 0.020(6) 0.167(6) 0.062(16) Uiso 1 1 d . . .
Eu1 Eu 0.291781(17) -0.203997(15) 0.195535(15) 0.01245(5) Uani 1 1 d . . .
O1 O 0.3731(3) 0.0819(2) 0.3666(2) 0.0178(4) Uani 1 1 d . . .
O2 O 0.6228(3) -0.1269(3) 0.3234(3) 0.0200(4) Uani 1 1 d . . .
O3 O 0.6341(3) 0.2126(2) 0.5754(2) 0.0190(4) Uani 1 1 d . . .
O4 O 0.0143(3) -0.2748(3) 0.2380(3) 0.0234(5) Uani 1 1 d . . .
O5 O 0.3393(3) 0.5408(2) 0.0955(3) 0.0208(4) Uani 1 1 d . . .
O6 O 0.0656(3) -0.3777(3) -0.0694(3) 0.0235(5) Uani 1 1 d . . .
O7 O 0.4235(4) -0.1289(3) 0.0486(3) 0.0245(5) Uani 1 1 d . . .
O8 O 0.0681(4) -0.0772(3) 0.1009(3) 0.0265(5) Uani 1 1 d . . .
O11 O 0.2773(3) 0.2750(2) -0.0288(2) 0.0195(4) Uani 1 1 d . . .
N1 N 1.0063(3) 0.7905(3) 0.5372(3) 0.0186(5) Uani 1 1 d . . .
N2 N 1.1537(3) 0.8913(3) 0.6679(3) 0.0199(5) Uani 1 1 d . . .
N3 N 1.1661(3) 0.8532(3) 0.7751(3) 0.0200(5) Uani 1 1 d . . .
N4 N 1.0246(3) 0.7263(3) 0.7180(3) 0.0188(5) Uani 1 1 d . . .
C1 C 0.5208(4) 0.1939(3) 0.4517(3) 0.0133(5) Uani 1 1 d . . .
C2 C 0.5635(4) 0.3143(3) 0.4056(3) 0.0132(5) Uani 1 1 d . . .
C3 C 0.4487(4) 0.3016(3) 0.2670(3) 0.0149(5) Uani 1 1 d . . .
C4 C 0.4895(4) 0.4192(3) 0.2317(3) 0.0140(5) Uani 1 1 d . . .
C5 C 0.6475(4) 0.5461(3) 0.3299(3) 0.0144(5) Uani 1 1 d . . .
C6 C 0.7642(4) 0.5565(3) 0.4650(3) 0.0142(5) Uani 1 1 d . . .
C7 C 0.7196(4) 0.4413(3) 0.5033(3) 0.0151(5) Uani 1 1 d . . .
C8 C 0.9301(4) 0.6900(3) 0.5722(3) 0.0150(5) Uani 1 1 d . . .
C9 C 0.3594(4) 0.4115(3) 0.0892(3) 0.0149(5) Uani 1 1 d . . .
H8 H 0.340(4) 0.218(4) 0.204(4) 0.014(8) Uiso 1 1 d . . .
H4 H -0.085(7) -0.280(6) 0.184(6) 0.051(14) Uiso 1 1 d . . .
H7 H 0.795(5) 0.447(4) 0.592(4) 0.022(9) Uiso 1 1 d . . .
H2 H 0.679(6) -0.064(5) 0.326(5) 0.030(12) Uiso 1 1 d . . .
H9 H 0.670(5) 0.619(4) 0.303(4) 0.019(8) Uiso 1 1 d . . .
H5 H 0.059(6) -0.463(5) -0.113(5) 0.031(12) Uiso 1 1 d . . .
H6 H 0.041(5) -0.351(5) -0.138(5) 0.027(10) Uiso 1 1 d . . .
H1 H 0.657(7) -0.101(6) 0.410(7) 0.056(16) Uiso 1 1 d . . .
H13 H 0.361(6) -0.123(5) -0.024(6) 0.044(13) Uiso 1 1 d . . .
H12 H 0.512(7) -0.146(6) 0.042(6) 0.052(15) Uiso 1 1 d . . .
H3 H 0.020(6) -0.240(5) 0.323(6) 0.034(12) 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
Eu1 O3 2.3230(19) 2_656 ?
Eu1 O5 2.346(2) 1_545 ?
Eu1 O7 2.409(2) . ?
Eu1 O1 2.416(2) . ?
Eu1 O2 2.434(2) . ?
Eu1 O6 2.439(2) . ?
Eu1 O4 2.477(2) . ?
Eu1 O8 2.484(2) . ?
O1 C1 1.271(3) . ?
O2 H2 0.71(4) . ?
O2 H1 0.77(6) . ?
O3 C1 1.253(3) . ?
O3 Eu1 2.3230(19) 2_656 ?
O4 H4 0.81(5) . ?
O4 H3 0.78(5) . ?
O5 C9 1.262(3) . ?
O5 Eu1 2.346(2) 1_565 ?
O6 H5 0.73(4) . ?
O6 H6 0.84(4) . ?
O7 H13 0.80(5) . ?
O7 H12 0.76(5) . ?
O8 H10 0.73(5) . ?
O8 H11 0.84(5) . ?
O11 C9 1.258(3) . ?
N1 C8 1.341(3) . ?
N1 N2 1.346(3) . ?
N2 N3 1.307(3) . ?
N3 N4 1.348(3) . ?
N4 C8 1.334(4) . ?
C1 C2 1.500(4) . ?
C2 C7 1.387(4) . ?
C2 C3 1.402(4) . ?
C3 C4 1.390(4) . ?
C3 H8 0.94(3) . ?
C4 C5 1.396(4) . ?
C4 C9 1.500(4) . ?
C5 C6 1.389(4) . ?
C5 H9 0.89(4) . ?
C6 C7 1.399(4) . ?
C6 C8 1.469(4) . ?
C7 H7 0.91(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
O3 Eu1 O5 83.18(7) 2_656 1_545 ?
O3 Eu1 O7 142.65(8) 2_656 . ?
O5 Eu1 O7 94.78(8) 1_545 . ?
O3 Eu1 O1 84.53(7) 2_656 . ?
O5 Eu1 O1 156.06(7) 1_545 . ?
O7 Eu1 O1 82.76(8) . . ?
O3 Eu1 O2 71.63(8) 2_656 . ?
O5 Eu1 O2 81.10(8) 1_545 . ?
O7 Eu1 O2 71.23(9) . . ?
O1 Eu1 O2 75.56(7) . . ?
O3 Eu1 O6 133.98(8) 2_656 . ?
O5 Eu1 O6 70.78(8) 1_545 . ?
O7 Eu1 O6 78.46(8) . . ?
O1 Eu1 O6 131.17(7) . . ?
O2 Eu1 O6 136.36(8) . . ?
O3 Eu1 O4 68.79(8) 2_656 . ?
O5 Eu1 O4 96.62(8) 1_545 . ?
O7 Eu1 O4 147.83(8) . . ?
O1 Eu1 O4 97.95(8) . . ?
O2 Eu1 O4 140.33(8) . . ?
O6 Eu1 O4 77.12(8) . . ?
O3 Eu1 O8 127.60(8) 2_656 . ?
O5 Eu1 O8 135.82(8) 1_545 . ?
O7 Eu1 O8 78.33(9) . . ?
O1 Eu1 O8 67.17(8) . . ?
O2 Eu1 O8 134.16(8) . . ?
O6 Eu1 O8 65.06(9) . . ?
O4 Eu1 O8 72.54(8) . . ?
C1 O1 Eu1 135.82(18) . . ?
Eu1 O2 H2 122(3) . . ?
Eu1 O2 H1 114(4) . . ?
H2 O2 H1 101(5) . . ?
C1 O3 Eu1 152.06(18) . 2_656 ?
Eu1 O4 H4 122(3) . . ?
Eu1 O4 H3 119(3) . . ?
H4 O4 H3 108(5) . . ?
C9 O5 Eu1 158.0(2) . 1_565 ?
Eu1 O6 H5 121(3) . . ?
Eu1 O6 H6 124(3) . . ?
H5 O6 H6 104(4) . . ?
Eu1 O7 H13 121(3) . . ?
Eu1 O7 H12 121(4) . . ?
H13 O7 H12 112(5) . . ?
Eu1 O8 H10 124(4) . . ?
Eu1 O8 H11 110(3) . . ?
H10 O8 H11 111(5) . . ?
C8 N1 N2 104.4(2) . . ?
N3 N2 N1 110.1(2) . . ?
N2 N3 N4 108.9(2) . . ?
C8 N4 N3 105.2(2) . . ?
O3 C1 O1 123.9(2) . . ?
O3 C1 C2 116.9(2) . . ?
O1 C1 C2 119.2(2) . . ?
C7 C2 C3 119.5(2) . . ?
C7 C2 C1 119.0(2) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H8 121.0(19) . . ?
C2 C3 H8 119(2) . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 C9 119.5(2) . . ?
C5 C4 C9 119.9(2) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H9 122(2) . . ?
C4 C5 H9 118(2) . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 C8 121.3(2) . . ?
C7 C6 C8 119.2(2) . . ?
C2 C7 C6 120.8(3) . . ?
C2 C7 H7 119(2) . . ?
C6 C7 H7 120(2) . . ?
N4 C8 N1 111.2(2) . . ?
N4 C8 C6 123.8(2) . . ?
N1 C8 C6 124.9(3) . . ?
O11 C9 O5 124.6(3) . . ?
O11 C9 C4 117.1(2) . . ?
O5 C9 C4 118.3(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H3 N1 0.78(5) 2.15(5) 2.909(4) 164(4) 1_445
O7 H12 O11 0.76(5) 2.20(5) 2.911(3) 158(5) 2_655
O2 H1 O1 0.77(6) 2.33(6) 3.045(3) 154(5) 2_656
O7 H13 N3 0.80(5) 2.10(5) 2.890(3) 170(4) 1_444
O6 H6 N4 0.84(4) 1.94(4) 2.774(3) 171(4) 1_444
O6 H5 O4 0.73(4) 2.19(4) 2.917(4) 169(4) 2_545
O2 H2 N2 0.71(4) 2.00(4) 2.716(3) 177(4) 2_766
O4 H4 O11 0.81(5) 1.89(5) 2.670(3) 163(5) 2
O8 H11 N4 0.84(5) 2.64(5) 3.365(4) 146(4) 2_666
O8 H11 N3 0.84(5) 2.62(5) 3.104(4) 118(4) 2_666

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.385
_refine_diff_density_min         -1.310
_refine_diff_density_rms         0.124
_exptl_crystal_recrystallization_method hydrothermal
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/cc13jszd
_database_code_depnum_ccdc_archive 'CCDC 1029044'
_audit_update_record             
;
2014-10-14 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 N4 O9 Sm'
_chemical_formula_weight         471.59

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           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.9849(16)
_cell_length_b                   9.783(2)
_cell_length_c                   10.443(2)
_cell_angle_alpha                116.75(3)
_cell_angle_beta                 107.36(3)
_cell_angle_gamma                95.71(3)
_cell_volume                     668.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'colorless '
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             458
_exptl_absorpt_coefficient_mu    4.452
_exptl_absorpt_correction_type   ?
_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            3788
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0375
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2361
_reflns_number_gt                2276
_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)+(0.0000P)²+1.8115P] 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         2361
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.572
_refine_ls_restrained_S_all      1.572
_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
Sm1 Sm 0.20849(4) 0.20413(3) 0.30467(3) 0.01346(11) Uani 1 1 d . . .
O1 O 0.2222(5) 0.7247(5) 0.5285(5) 0.0204(9) Uani 1 1 d . . .
O7 O 0.4346(7) 0.0785(6) 0.4007(6) 0.0277(10) Uani 1 1 d . . .
O6 O 0.0758(7) 0.1288(6) 0.4528(5) 0.0258(10) Uani 1 1 d . . .
O3 O 0.1268(5) 0.9177(5) 0.1334(5) 0.0190(9) Uani 1 1 d . . .
O5 O -0.1236(7) 0.1265(6) 0.1769(7) 0.0217(10) Uani 1 1 d . . .
O4 O -0.1330(6) 0.7873(5) -0.0746(5) 0.0201(9) Uani 1 1 d . . .
O9 O 0.4868(6) 0.2753(6) 0.2620(6) 0.0256(10) Uani 1 1 d . . .
O8 O 0.4349(6) 0.3784(6) 0.5713(5) 0.0251(10) Uani 1 1 d . . .
O2 O 0.1598(6) 0.4595(5) 0.4045(5) 0.0226(9) Uani 1 1 d . . .
C2 C 0.0100(8) 0.5806(7) 0.2679(6) 0.0157(11) Uani 1 1 d . . .
N4 N -0.5054(7) 0.2097(6) -0.0375(6) 0.0203(11) Uani 1 1 d . . .
N3 N -0.6533(7) 0.1088(6) -0.1672(6) 0.0207(11) Uani 1 1 d . . .
N2 N -0.6654(7) 0.1481(6) -0.2738(6) 0.0204(11) Uani 1 1 d . . .
N1 N -0.5243(7) 0.2742(6) -0.2177(6) 0.0189(10) Uani 1 1 d . . .
C8 C -0.4291(7) 0.3102(7) -0.0717(6) 0.0145(11) Uani 1 1 d . . .
C7 C -0.0203(7) 0.8053(6) 0.0484(6) 0.0136(11) Uani 1 1 d . . .
C5 C -0.0635(7) 0.6850(6) 0.0940(6) 0.0134(11) Uani 1 1 d . . .
C4 C -0.2198(8) 0.5591(7) -0.0029(6) 0.0154(11) Uani 1 1 d . . .
H14 H -0.2967 0.5512 -0.0941 0.018 Uiso 1 1 calc R . .
C3 C -0.1471(7) 0.4545(7) 0.1703(6) 0.0150(11) Uani 1 1 d . . .
H15 H -0.1748 0.3774 0.1953 0.018 Uiso 1 1 calc R . .
C9 C -0.2631(8) 0.4441(7) 0.0346(6) 0.0150(11) Uani 1 1 d . . .
C1 C 0.1402(8) 0.5893(7) 0.4109(7) 0.0154(12) Uani 1 1 d . . .
C6 C 0.0507(8) 0.6983(7) 0.2327(6) 0.0158(11) Uani 1 1 d . . .
H16 H 0.1530 0.7851 0.3008 0.019 Uiso 1 1 calc R . .
H3 H 0.439(9) 0.471(9) 0.618(8) 0.016(17) Uiso 1 1 d . . .
H4 H 0.456(11) 0.346(10) 0.648(10) 0.04(2) Uiso 1 1 d . . .
H2 H 0.574(13) 0.265(11) 0.307(11) 0.05(3) Uiso 1 1 d . . .
H1 H 0.488(11) 0.247(10) 0.164(11) 0.05(2) Uiso 1 1 d . . .
H6 H -0.185(12) 0.061(11) 0.179(10) 0.04(3) Uiso 1 1 d . . .
H5 H -0.150(12) 0.113(10) 0.113(10) 0.02(3) Uiso 1 1 d . . .
H9 H 0.128(13) 0.121(11) 0.530(12) 0.06(3) Uiso 1 1 d . . .
H7 H 0.546(16) 0.120(13) 0.440(13) 0.07(4) Uiso 1 1 d . . .
H8 H 0.418(15) -0.011(14) 0.343(14) 0.08(4) Uiso 1 1 d . . .
H10 H -0.020(18) 0.144(15) 0.467(15) 0.10(4) 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 O4 2.339(4) 2_565 ?
Sm1 O2 2.360(4) . ?
Sm1 O3 2.430(4) 1_545 ?
Sm1 O6 2.431(4) . ?
Sm1 O5 2.442(5) . ?
Sm1 O8 2.457(5) . ?
Sm1 O9 2.487(5) . ?
Sm1 O7 2.500(5) . ?
O1 C1 1.255(7) . ?
O7 H7 0.83(12) . ?
O7 H8 0.78(12) . ?
O6 H9 0.83(10) . ?
O6 H10 0.84(14) . ?
O3 C7 1.273(7) . ?
O3 Sm1 2.430(4) 1_565 ?
O5 H6 0.78(9) . ?
O5 H5 0.58(8) . ?
O4 C7 1.252(7) . ?
O4 Sm1 2.339(4) 2_565 ?
O9 H2 0.76(9) . ?
O9 H1 0.94(10) . ?
O8 H3 0.81(7) . ?
O8 H4 0.96(9) . ?
O2 C1 1.269(7) . ?
C2 C3 1.390(8) . ?
C2 C6 1.395(8) . ?
C2 C1 1.503(8) . ?
N4 C8 1.339(7) . ?
N4 N3 1.347(7) . ?
N3 N2 1.314(7) . ?
N2 N1 1.347(7) . ?
N1 C8 1.341(7) . ?
C8 C9 1.474(8) . ?
C7 C5 1.501(8) . ?
C5 C4 1.385(8) . ?
C5 C6 1.402(8) . ?
C4 C9 1.392(8) . ?
C4 H14 0.9300 . ?
C3 C9 1.394(8) . ?
C3 H15 0.9300 . ?
C6 H16 0.9300 . ?

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
O4 Sm1 O2 83.10(15) 2_565 . ?
O4 Sm1 O3 84.52(14) 2_565 1_545 ?
O2 Sm1 O3 155.93(14) . 1_545 ?
O4 Sm1 O6 142.53(16) 2_565 . ?
O2 Sm1 O6 94.68(16) . . ?
O3 Sm1 O6 82.82(15) 1_545 . ?
O4 Sm1 O5 71.56(18) 2_565 . ?
O2 Sm1 O5 81.03(16) . . ?
O3 Sm1 O5 75.50(16) 1_545 . ?
O6 Sm1 O5 71.15(19) . . ?
O4 Sm1 O8 134.31(15) 2_565 . ?
O2 Sm1 O8 70.81(16) . . ?
O3 Sm1 O8 131.19(15) 1_545 . ?
O6 Sm1 O8 78.11(16) . . ?
O5 Sm1 O8 136.03(18) . . ?
O4 Sm1 O9 68.87(16) 2_565 . ?
O2 Sm1 O9 96.66(16) . . ?
O3 Sm1 O9 97.99(16) 1_545 . ?
O6 Sm1 O9 147.90(17) . . ?
O5 Sm1 O9 140.35(19) . . ?
O8 Sm1 O9 77.49(16) . . ?
O4 Sm1 O7 127.78(16) 2_565 . ?
O2 Sm1 O7 135.68(17) . . ?
O3 Sm1 O7 67.44(16) 1_545 . ?
O6 Sm1 O7 78.42(17) . . ?
O5 Sm1 O7 134.31(18) . . ?
O8 Sm1 O7 64.90(18) . . ?
O9 Sm1 O7 72.49(17) . . ?
Sm1 O7 H7 123(7) . . ?
Sm1 O7 H8 115(8) . . ?
H7 O7 H8 107(10) . . ?
Sm1 O6 H9 129(7) . . ?
Sm1 O6 H10 128(9) . . ?
H9 O6 H10 99(10) . . ?
C7 O3 Sm1 136.2(4) . 1_565 ?
Sm1 O5 H6 121(6) . . ?
Sm1 O5 H5 114(9) . . ?
H6 O5 H5 107(10) . . ?
C7 O4 Sm1 152.4(4) . 2_565 ?
Sm1 O9 H2 117(7) . . ?
Sm1 O9 H1 124(5) . . ?
H2 O9 H1 107(9) . . ?
Sm1 O8 H3 120(5) . . ?
Sm1 O8 H4 121(5) . . ?
H3 O8 H4 105(7) . . ?
C1 O2 Sm1 158.0(4) . . ?
C3 C2 C6 120.5(5) . . ?
C3 C2 C1 120.2(5) . . ?
C6 C2 C1 119.3(5) . . ?
C8 N4 N3 105.1(5) . . ?
N2 N3 N4 109.4(5) . . ?
N3 N2 N1 109.5(5) . . ?
C8 N1 N2 105.0(5) . . ?
N4 C8 N1 111.1(5) . . ?
N4 C8 C9 125.6(5) . . ?
N1 C8 C9 123.4(5) . . ?
O4 C7 O3 123.4(5) . . ?
O4 C7 C5 117.0(5) . . ?
O3 C7 C5 119.6(5) . . ?
C4 C5 C6 119.6(5) . . ?
C4 C5 C7 119.1(5) . . ?
C6 C5 C7 121.3(5) . . ?
C5 C4 C9 120.7(5) . . ?
C5 C4 H14 119.6 . . ?
C9 C4 H14 119.6 . . ?
C2 C3 C9 119.7(5) . . ?
C2 C3 H15 120.1 . . ?
C9 C3 H15 120.1 . . ?
C4 C9 C3 119.8(5) . . ?
C4 C9 C8 119.6(5) . . ?
C3 C9 C8 120.6(5) . . ?
O1 C1 O2 124.5(5) . . ?
O1 C1 C2 117.6(5) . . ?
O2 C1 C2 117.8(5) . . ?
C2 C6 C5 119.6(5) . . ?
C2 C6 H16 120.2 . . ?
C5 C6 H16 120.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H3 O9 0.81(7) 2.13(7) 2.918(7) 167(6) 2_666
O8 H4 N1 0.96(9) 1.81(9) 2.767(7) 175(7) 1_656
O8 H4 N2 0.96(9) 2.62(9) 3.468(7) 147(6) 1_656
O9 H2 O1 0.76(9) 1.93(10) 2.674(6) 164(10) 2_666
O9 H1 N4 0.94(10) 1.99(10) 2.917(7) 175(7) 1_655
O5 H6 N3 0.78(9) 1.93(10) 2.712(7) 175(9) 2_455
O5 H5 O3 0.58(8) 2.52(9) 3.061(8) 157(11) 2_565
O6 H9 N2 0.83(10) 2.10(10) 2.894(7) 161(9) 1_656
O7 H7 O1 0.83(12) 2.11(12) 2.868(7) 151(10) 2_666
O7 H8 N2 0.78(12) 2.59(11) 3.112(7) 126(10) 2
O7 H8 N1 0.78(12) 2.67(12) 3.382(7) 154(10) 2
O6 H10 O1 0.84(14) 2.15(13) 2.908(7) 149(12) 2_566

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.780
_refine_diff_density_min         -1.354
_refine_diff_density_rms         0.125
_exptl_crystal_recrystallization_method hydrothermal
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_JJ
_audit_block_doi                 10.5517/cc13ptzl
_database_code_depnum_ccdc_archive 'CCDC 1033880'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 Gd N4 O9'
_chemical_formula_weight         478.48

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'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.9767(5)
_cell_length_b                   9.7325(5)
_cell_length_c                   10.3966(6)
_cell_angle_alpha                116.8210(10)
_cell_angle_beta                 107.3330(10)
_cell_angle_gamma                95.6690(10)
_cell_volume                     661.32(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_F_000             462
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    5.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4839
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.395
_diffrn_reflns_theta_max         28.283
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3218
_reflns_number_gt                3065
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3218
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7198(5) 0.4417(4) 0.5032(4) 0.0148(6) Uani 1 1 d . . . . .
H11 H 0.7957 0.4505 0.5955 0.018 Uiso 1 1 calc R U . . .
C2 C 0.7649(5) 0.5573(4) 0.4661(4) 0.0135(6) Uani 1 1 d . . . . .
C3 C 0.6478(5) 0.5463(4) 0.3296(4) 0.0146(6) Uani 1 1 d . . . . .
H12 H 0.6755 0.6232 0.3038 0.018 Uiso 1 1 calc R U . . .
C4 C 0.4895(5) 0.4200(4) 0.2324(4) 0.0140(6) Uani 1 1 d . . . . .
C9 C 0.3595(5) 0.4119(4) 0.0894(4) 0.0146(6) Uani 1 1 d . . . . .
C10 C 0.5209(5) 1.1940(4) 0.4518(4) 0.0117(6) Uani 1 1 d . . . . .
C6 C 0.9307(5) 0.6913(4) 0.5731(4) 0.0147(6) Uani 1 1 d . . . . .
C7 C 0.5645(5) 0.3141(4) 0.4057(4) 0.0137(6) Uani 1 1 d . . . . .
C8 C 0.4493(5) 0.3024(4) 0.2674(4) 0.0159(7) Uani 1 1 d . . . . .
H13 H 0.3463 0.2159 0.1994 0.019 Uiso 1 1 calc R U . . .
Gd1 Gd 0.29191(2) 0.79641(2) 0.19585(2) 0.01232(8) Uani 1 1 d . . . . .
H1 H 0.659(11) 0.893(10) 0.402(10) 0.07(3) Uiso 1 1 d . . . . .
H2 H 0.676(9) 0.950(8) 0.343(8) 0.05(2) Uiso 1 1 d . . . . .
H3 H 0.512(9) 0.849(7) 0.038(7) 0.029(15) Uiso 1 1 d . . . . .
H4 H 0.369(7) 0.872(6) -0.034(7) 0.027(13) Uiso 1 1 d . . . . .
H5 H 0.073(9) 0.990(7) 0.153(7) 0.032(18) Uiso 1 1 d . . . . .
H6 H -0.064(13) 0.859(11) 0.004(11) 0.09(3) Uiso 1 1 d . . . . .
H7 H 0.044(8) 0.664(7) -0.150(7) 0.043(16) Uiso 1 1 d . . . . .
H8 H 0.068(8) 0.528(7) -0.132(7) 0.035(15) Uiso 1 1 d . . . . .
H9 H -0.093(11) 0.725(9) 0.188(9) 0.06(2) Uiso 1 1 d . . . . .
H10 H 0.024(7) 0.753(6) 0.331(7) 0.019(12) Uiso 1 1 d . . . . .
N1 N 1.1544(5) 0.8925(4) 0.6685(4) 0.0202(6) Uani 1 1 d . . . . .
N2 N 1.1663(5) 0.8533(4) 0.7758(4) 0.0194(6) Uani 1 1 d . . . . .
N3 N 1.0263(4) 0.7275(4) 0.7197(4) 0.0190(6) Uani 1 1 d . . . . .
N4 N 1.0061(4) 0.7913(4) 0.5376(4) 0.0186(6) Uani 1 1 d . . . . .
O1 O 0.6212(4) 0.8727(3) 0.3227(4) 0.0192(5) Uani 1 1 d . . . . .
O2 O 0.3652(4) 0.7872(3) 0.4244(3) 0.0184(5) Uani 1 1 d . . . . .
O3 O 0.0162(4) 0.7256(4) 0.2376(4) 0.0238(6) Uani 1 1 d . . . . .
O4 O 0.3401(4) 0.5418(3) 0.0959(3) 0.0215(6) Uani 1 1 d . . . . .
O5 O 0.0656(4) 0.6226(3) -0.0689(3) 0.0237(6) Uani 1 1 d . . . . .
O6 O 0.0703(5) 0.9230(4) 0.1013(4) 0.0268(7) Uani 1 1 d . . . . .
O7 O 0.4232(5) 0.8702(4) 0.0489(4) 0.0241(6) Uani 1 1 d . . . . .
O8 O 0.3736(4) 1.0818(3) 0.3665(3) 0.0188(5) Uani 1 1 d . . . . .
O9 O 0.2764(4) 0.2750(3) -0.0291(3) 0.0201(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
C1 C7 1.384(5) . ?
C1 C2 1.392(5) . ?
C2 C3 1.397(5) . ?
C2 C6 1.470(5) . ?
C3 C4 1.392(5) . ?
C4 C8 1.385(5) . ?
C4 C9 1.500(5) . ?
C9 O9 1.261(4) . ?
C9 O4 1.263(4) . ?
C10 O2 1.255(4) 2_676 ?
C10 O8 1.270(4) . ?
C10 C7 1.497(4) 1_565 ?
C6 N4 1.338(4) . ?
C6 N3 1.341(5) . ?
C7 C8 1.403(5) . ?
C7 C10 1.497(4) 1_545 ?
Gd1 O2 2.317(3) . ?
Gd1 O4 2.338(3) . ?
Gd1 O7 2.396(3) . ?
Gd1 O8 2.407(3) . ?
Gd1 O1 2.420(3) . ?
Gd1 O5 2.436(3) . ?
Gd1 O3 2.457(3) . ?
Gd1 O6 2.469(3) . ?
N1 N2 1.314(5) . ?
N1 N4 1.350(5) . ?
N2 N3 1.336(4) . ?
O2 C10 1.255(4) 2_676 ?

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
C7 C1 C2 121.5(3) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 C6 119.7(3) . . ?
C3 C2 C6 121.2(3) . . ?
C4 C3 C2 119.8(3) . . ?
C8 C4 C3 120.6(3) . . ?
C8 C4 C9 119.5(3) . . ?
C3 C4 C9 119.9(3) . . ?
O9 C9 O4 124.5(3) . . ?
O9 C9 C4 117.4(3) . . ?
O4 C9 C4 118.1(3) . . ?
O2 C10 O8 124.0(3) 2_676 . ?
O2 C10 C7 116.6(3) 2_676 1_565 ?
O8 C10 C7 119.4(3) . 1_565 ?
N4 C6 N3 111.5(3) . . ?
N4 C6 C2 124.9(3) . . ?
N3 C6 C2 123.7(3) . . ?
C1 C7 C8 119.1(3) . . ?
C1 C7 C10 119.4(3) . 1_545 ?
C8 C7 C10 121.5(3) . 1_545 ?
C4 C8 C7 119.9(3) . . ?
O2 Gd1 O4 83.14(10) . . ?
O2 Gd1 O7 142.77(11) . . ?
O4 Gd1 O7 94.43(11) . . ?
O2 Gd1 O8 84.66(9) . . ?
O4 Gd1 O8 155.86(10) . . ?
O7 Gd1 O8 82.88(10) . . ?
O2 Gd1 O1 71.82(10) . . ?
O4 Gd1 O1 80.87(10) . . ?
O7 Gd1 O1 71.13(11) . . ?
O8 Gd1 O1 75.55(9) . . ?
O2 Gd1 O5 133.75(9) . . ?
O4 Gd1 O5 70.88(10) . . ?
O7 Gd1 O5 78.48(10) . . ?
O8 Gd1 O5 131.22(10) . . ?
O1 Gd1 O5 136.35(11) . . ?
O2 Gd1 O3 68.74(10) . . ?
O4 Gd1 O3 96.69(10) . . ?
O7 Gd1 O3 147.85(11) . . ?
O8 Gd1 O3 98.19(10) . . ?
O1 Gd1 O3 140.48(11) . . ?
O5 Gd1 O3 76.90(11) . . ?
O2 Gd1 O6 127.75(11) . . ?
O4 Gd1 O6 135.89(11) . . ?
O7 Gd1 O6 78.28(12) . . ?
O8 Gd1 O6 67.21(11) . . ?
O1 Gd1 O6 134.05(11) . . ?
O5 Gd1 O6 65.03(11) . . ?
O3 Gd1 O6 72.76(11) . . ?
N2 N1 N4 109.7(3) . . ?
N1 N2 N3 109.4(3) . . ?
N2 N3 C6 105.1(3) . . ?
C6 N4 N1 104.3(3) . . ?
C10 O2 Gd1 151.7(2) 2_676 . ?
C9 O4 Gd1 157.9(3) . . ?
C10 O8 Gd1 136.1(2) . . ?

_refine_diff_density_max         1.313
_refine_diff_density_min         -1.199
_refine_diff_density_rms         0.179


_exptl_crystal_recrystallization_method hydrothermal
_exptl_crystal_preparation       Luminescent
