# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

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# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_050810b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H13 N6 O13 Pr'
_chemical_formula_weight         542.15

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'
Pr Pr -0.2180 2.8214 '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                   16.477(3)
_cell_length_b                   6.8521(11)
_cell_length_c                   14.560(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.789(2)
_cell_angle_gamma                90.00
_cell_volume                     1609.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5394
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      26.79

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064
_exptl_absorpt_coefficient_mu    3.117
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.682009
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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            8813
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         26.79
_reflns_number_total             3395
_reflns_number_gt                2942
_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)+(0.0375P)²+2.4550P] 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         3395
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Pr1 Pr 0.181204(11) 0.64011(3) 0.295108(14) 0.01622(8) Uani 1 1 d . . .
O1 O 0.32700(18) 0.7526(5) 0.3370(3) 0.0441(9) Uani 1 1 d . . .
O2 O 0.4146(2) 0.7287(6) 0.4742(2) 0.0452(9) Uani 1 1 d . . .
O3 O 0.5667(2) 0.7715(6) 0.5374(3) 0.0500(9) Uani 1 1 d . . .
H3 H 0.5171 0.7544 0.5167 0.075 Uiso 1 1 calc R . .
O4 O 0.6774(2) 0.8563(5) 0.4842(3) 0.0522(11) Uani 1 1 d . . .
O5 O 0.03410(16) 0.7426(4) 0.30635(18) 0.0235(6) Uani 1 1 d . . .
O6 O -0.09281(17) 0.8533(4) 0.2488(2) 0.0230(6) Uani 1 1 d . . .
O7 O -0.17385(17) 0.9778(5) 0.0610(2) 0.0310(7) Uani 1 1 d . . .
O8 O -0.1650(2) 0.8318(5) -0.0725(2) 0.0338(7) Uani 1 1 d . . .
O9 O 0.19171(19) 0.8941(5) 0.4265(2) 0.0326(7) Uani 1 1 d . . .
H9A H 0.2401 0.9386 0.4472 0.039 Uiso 1 1 d R . .
H9B H 0.1626 0.8688 0.4670 0.039 Uiso 1 1 d R . .
O10 O 0.1865(2) 0.9775(4) 0.2371(2) 0.0381(8) Uani 1 1 d . . .
H10A H 0.1900 1.0680 0.2776 0.046 Uiso 1 1 d R . .
H10B H 0.1775 1.0249 0.1821 0.046 Uiso 1 1 d R . .
O11 O 0.2784(2) 0.3338(5) 0.3224(3) 0.0444(9) Uani 1 1 d . . .
H11A H 0.3212 0.3473 0.2990 0.053 Uiso 1 1 d R . .
H11B H 0.2855 0.2872 0.3775 0.053 Uiso 1 1 d R . .
O12 O 0.2350(2) 0.5454(7) 0.1543(2) 0.0507(10) Uani 1 1 d . . .
H12A H 0.2727 0.4620 0.1725 0.061 Uiso 1 1 d R . .
H12B H 0.2481 0.6470 0.1273 0.061 Uiso 1 1 d R . .
N1 N 0.4536(2) 0.8762(5) 0.2518(3) 0.0320(9) Uani 1 1 d . . .
H1 H 0.4058 0.8799 0.2146 0.038 Uiso 1 1 calc R . .
N2 N 0.5251(3) 0.9144(7) 0.2260(3) 0.0457(11) Uani 1 1 d . . .
N3 N 0.5846(2) 0.8991(6) 0.3004(3) 0.0416(10) Uani 1 1 d . . .
N4 N 0.06981(19) 0.7044(5) 0.1344(2) 0.0207(7) Uani 1 1 d . . .
N5 N 0.0733(2) 0.6905(5) 0.0455(2) 0.0235(7) Uani 1 1 d . . .
N6 N -0.0007(2) 0.7460(5) -0.0034(2) 0.0227(7) Uani 1 1 d . . .
H6 H -0.0139 0.7477 -0.0637 0.027 Uiso 1 1 calc R . .
C1 C 0.3965(2) 0.7672(6) 0.3878(3) 0.0290(9) Uani 1 1 d . . .
C2 C 0.4657(3) 0.8314(6) 0.3433(3) 0.0249(9) Uani 1 1 d . . .
C3 C 0.5502(3) 0.8493(6) 0.3744(3) 0.0284(9) Uani 1 1 d . . .
C4 C 0.6027(3) 0.8247(7) 0.4693(4) 0.0366(11) Uani 1 1 d . . .
C5 C -0.0238(2) 0.7929(5) 0.2390(2) 0.0169(7) Uani 1 1 d . . .
C6 C -0.0062(2) 0.7709(6) 0.1430(3) 0.0180(7) Uani 1 1 d . . .
C7 C -0.0525(2) 0.7990(6) 0.0533(3) 0.0182(7) Uani 1 1 d . . .
C8 C -0.1376(2) 0.8749(5) 0.0109(3) 0.0210(8) Uani 1 1 d . . .
O13 O 0.3252(2) 0.9059(6) 0.1008(2) 0.0516(10) Uani 1 1 d . . .
H13A H 0.3425 0.8685 0.0525 0.062 Uiso 1 1 d R . .
H13B H 0.2882 0.9940 0.0929 0.062 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
Pr1 O7 2.397(3) 2_545 ?
Pr1 O6 2.452(3) 2_545 ?
Pr1 O10 2.469(3) . ?
Pr1 O1 2.478(3) . ?
Pr1 O12 2.481(3) . ?
Pr1 O5 2.561(3) . ?
Pr1 O9 2.566(3) . ?
Pr1 O11 2.620(3) . ?
Pr1 N4 2.699(3) . ?
O1 C1 1.234(5) . ?
O2 C1 1.260(6) . ?
O3 C4 1.307(6) . ?
O3 H3 0.8200 . ?
O4 C4 1.224(6) . ?
O5 C5 1.268(4) . ?
O6 C5 1.246(4) . ?
O6 Pr1 2.452(3) 2 ?
O7 C8 1.250(5) . ?
O7 Pr1 2.397(3) 2 ?
O8 C8 1.242(5) . ?
O9 H9A 0.8484 . ?
O9 H9B 0.8504 . ?
O10 H10A 0.8503 . ?
O10 H10B 0.8483 . ?
O11 H11A 0.8497 . ?
O11 H11B 0.8485 . ?
O12 H12A 0.8468 . ?
O12 H12B 0.8486 . ?
N1 N2 1.334(6) . ?
N1 C2 1.341(6) . ?
N1 H1 0.8600 . ?
N2 N3 1.309(6) . ?
N3 C3 1.359(6) . ?
N4 N5 1.311(5) . ?
N4 C6 1.362(5) . ?
N5 N6 1.336(5) . ?
N6 C7 1.352(5) . ?
N6 H6 0.8600 . ?
C1 C2 1.488(6) . ?
C2 C3 1.380(6) . ?
C3 C4 1.481(7) . ?
C5 C6 1.493(5) . ?
C6 C7 1.384(5) . ?
C7 C8 1.505(5) . ?
O13 H13A 0.8505 . ?
O13 H13B 0.8492 . ?

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
O7 Pr1 O6 73.90(10) 2_545 2_545 ?
O7 Pr1 O10 138.18(11) 2_545 . ?
O6 Pr1 O10 136.20(10) 2_545 . ?
O7 Pr1 O1 98.55(11) 2_545 . ?
O6 Pr1 O1 143.90(11) 2_545 . ?
O10 Pr1 O1 72.11(11) . . ?
O7 Pr1 O12 133.76(13) 2_545 . ?
O6 Pr1 O12 82.42(12) 2_545 . ?
O10 Pr1 O12 85.33(13) . . ?
O1 Pr1 O12 78.05(12) . . ?
O7 Pr1 O5 81.60(9) 2_545 . ?
O6 Pr1 O5 73.56(9) 2_545 . ?
O10 Pr1 O5 82.25(10) . . ?
O1 Pr1 O5 141.42(11) . . ?
O12 Pr1 O5 128.84(9) . . ?
O7 Pr1 O9 70.78(10) 2_545 . ?
O6 Pr1 O9 133.17(10) 2_545 . ?
O10 Pr1 O9 67.57(10) . . ?
O1 Pr1 O9 72.00(11) . . ?
O12 Pr1 O9 144.36(12) . . ?
O5 Pr1 O9 71.75(9) . . ?
O7 Pr1 O11 68.53(12) 2_545 . ?
O6 Pr1 O11 73.12(11) 2_545 . ?
O10 Pr1 O11 137.62(12) . . ?
O1 Pr1 O11 71.34(12) . . ?
O12 Pr1 O11 66.78(13) . . ?
O5 Pr1 O11 140.08(11) . . ?
O9 Pr1 O11 118.94(11) . . ?
O7 Pr1 N4 133.38(10) 2_545 . ?
O6 Pr1 N4 69.04(10) 2_545 . ?
O10 Pr1 N4 67.40(10) . . ?
O1 Pr1 N4 128.04(11) . . ?
O12 Pr1 N4 67.69(10) . . ?
O5 Pr1 N4 61.68(9) . . ?
O9 Pr1 N4 117.78(10) . . ?
O11 Pr1 N4 123.28(11) . . ?
C1 O1 Pr1 155.1(3) . . ?
C4 O3 H3 109.5 . . ?
C5 O5 Pr1 126.7(2) . . ?
C5 O6 Pr1 138.1(2) . 2 ?
C8 O7 Pr1 152.5(2) . 2 ?
Pr1 O9 H9A 115.0 . . ?
Pr1 O9 H9B 114.7 . . ?
H9A O9 H9B 116.7 . . ?
Pr1 O10 H10A 116.6 . . ?
Pr1 O10 H10B 132.1 . . ?
H10A O10 H10B 110.5 . . ?
Pr1 O11 H11A 112.6 . . ?
Pr1 O11 H11B 114.0 . . ?
H11A O11 H11B 117.0 . . ?
Pr1 O12 H12A 106.3 . . ?
Pr1 O12 H12B 109.6 . . ?
H12A O12 H12B 117.3 . . ?
N2 N1 C2 111.3(4) . . ?
N2 N1 H1 124.3 . . ?
C2 N1 H1 124.3 . . ?
N3 N2 N1 107.9(4) . . ?
N2 N3 C3 108.2(4) . . ?
N5 N4 C6 110.0(3) . . ?
N5 N4 Pr1 133.2(2) . . ?
C6 N4 Pr1 116.8(2) . . ?
N4 N5 N6 106.6(3) . . ?
N5 N6 C7 111.8(3) . . ?
N5 N6 H6 124.1 . . ?
C7 N6 H6 124.1 . . ?
O1 C1 O2 125.6(4) . . ?
O1 C1 C2 117.6(4) . . ?
O2 C1 C2 116.8(4) . . ?
N1 C2 C3 104.0(4) . . ?
N1 C2 C1 121.9(4) . . ?
C3 C2 C1 134.0(4) . . ?
N3 C3 C2 108.6(4) . . ?
N3 C3 C4 120.6(4) . . ?
C2 C3 C4 130.9(4) . . ?
O4 C4 O3 120.6(5) . . ?
O4 C4 C3 121.3(5) . . ?
O3 C4 C3 118.1(4) . . ?
O6 C5 O5 124.2(3) . . ?
O6 C5 C6 119.8(3) . . ?
O5 C5 C6 116.0(3) . . ?
N4 C6 C7 107.4(3) . . ?
N4 C6 C5 118.5(3) . . ?
C7 C6 C5 134.0(3) . . ?
N6 C7 C6 104.1(3) . . ?
N6 C7 C8 119.6(3) . . ?
C6 C7 C8 136.2(4) . . ?
O8 C8 O7 125.7(4) . . ?
O8 C8 C7 116.2(4) . . ?
O7 C8 C7 118.1(3) . . ?
H13A O13 H13B 117.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 Pr1 O1 C1 3.8(8) 2_545 . . . ?
O6 Pr1 O1 C1 -70.5(8) 2_545 . . . ?
O10 Pr1 O1 C1 141.9(8) . . . . ?
O12 Pr1 O1 C1 -129.2(8) . . . . ?
O5 Pr1 O1 C1 91.1(8) . . . . ?
O9 Pr1 O1 C1 70.3(8) . . . . ?
O11 Pr1 O1 C1 -60.0(8) . . . . ?
N4 Pr1 O1 C1 -178.1(7) . . . . ?
O7 Pr1 O5 C5 -156.1(3) 2_545 . . . ?
O6 Pr1 O5 C5 -80.5(3) 2_545 . . . ?
O10 Pr1 O5 C5 62.6(3) . . . . ?
O1 Pr1 O5 C5 110.7(3) . . . . ?
O12 Pr1 O5 C5 -14.9(4) . . . . ?
O9 Pr1 O5 C5 131.5(3) . . . . ?
O11 Pr1 O5 C5 -114.9(3) . . . . ?
N4 Pr1 O5 C5 -5.8(3) . . . . ?
C2 N1 N2 N3 -1.3(6) . . . . ?
N1 N2 N3 C3 0.3(6) . . . . ?
O7 Pr1 N4 N5 -135.7(3) 2_545 . . . ?
O6 Pr1 N4 N5 -96.1(4) 2_545 . . . ?
O10 Pr1 N4 N5 88.4(4) . . . . ?
O1 Pr1 N4 N5 46.9(4) . . . . ?
O12 Pr1 N4 N5 -5.9(3) . . . . ?
O5 Pr1 N4 N5 -178.2(4) . . . . ?
O9 Pr1 N4 N5 135.1(3) . . . . ?
O11 Pr1 N4 N5 -44.7(4) . . . . ?
O7 Pr1 N4 C6 46.6(3) 2_545 . . . ?
O6 Pr1 N4 C6 86.2(3) 2_545 . . . ?
O10 Pr1 N4 C6 -89.2(3) . . . . ?
O1 Pr1 N4 C6 -130.8(3) . . . . ?
O12 Pr1 N4 C6 176.5(3) . . . . ?
O5 Pr1 N4 C6 4.1(2) . . . . ?
O9 Pr1 N4 C6 -42.6(3) . . . . ?
O11 Pr1 N4 C6 137.6(3) . . . . ?
C6 N4 N5 N6 -0.7(4) . . . . ?
Pr1 N4 N5 N6 -178.4(3) . . . . ?
N4 N5 N6 C7 0.9(5) . . . . ?
Pr1 O1 C1 O2 -16.0(11) . . . . ?
Pr1 O1 C1 C2 162.4(6) . . . . ?
N2 N1 C2 C3 1.6(5) . . . . ?
N2 N1 C2 C1 -175.0(4) . . . . ?
O1 C1 C2 N1 1.4(6) . . . . ?
O2 C1 C2 N1 180.0(4) . . . . ?
O1 C1 C2 C3 -174.0(5) . . . . ?
O2 C1 C2 C3 4.6(7) . . . . ?
N2 N3 C3 C2 0.7(5) . . . . ?
N2 N3 C3 C4 -179.0(4) . . . . ?
N1 C2 C3 N3 -1.4(5) . . . . ?
C1 C2 C3 N3 174.6(5) . . . . ?
N1 C2 C3 C4 178.2(5) . . . . ?
C1 C2 C3 C4 -5.8(8) . . . . ?
N3 C3 C4 O4 3.1(7) . . . . ?
C2 C3 C4 O4 -176.4(4) . . . . ?
N3 C3 C4 O3 -178.1(4) . . . . ?
C2 C3 C4 O3 2.3(8) . . . . ?
Pr1 O6 C5 O5 124.7(4) 2 . . . ?
Pr1 O6 C5 C6 -57.1(5) 2 . . . ?
Pr1 O5 C5 O6 -175.3(3) . . . . ?
Pr1 O5 C5 C6 6.4(5) . . . . ?
N5 N4 C6 C7 0.2(4) . . . . ?
Pr1 N4 C6 C7 178.4(2) . . . . ?
N5 N4 C6 C5 178.6(3) . . . . ?
Pr1 N4 C6 C5 -3.2(4) . . . . ?
O6 C5 C6 N4 -179.9(3) . . . . ?
O5 C5 C6 N4 -1.6(5) . . . . ?
O6 C5 C6 C7 -2.1(7) . . . . ?
O5 C5 C6 C7 176.3(4) . . . . ?
N5 N6 C7 C6 -0.8(4) . . . . ?
N5 N6 C7 C8 177.2(3) . . . . ?
N4 C6 C7 N6 0.3(4) . . . . ?
C5 C6 C7 N6 -177.7(4) . . . . ?
N4 C6 C7 C8 -177.1(4) . . . . ?
C5 C6 C7 C8 4.8(8) . . . . ?
Pr1 O7 C8 O8 -177.6(4) 2 . . . ?
Pr1 O7 C8 C7 0.8(8) 2 . . . ?
N6 C7 C8 O8 20.6(5) . . . . ?
C6 C7 C8 O8 -162.2(4) . . . . ?
N6 C7 C8 O7 -157.9(4) . . . . ?
C6 C7 C8 O7 19.2(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.79
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         2.753
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.132
_database_code_depnum_ccdc_archive 'CCDC 287163'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_050926b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H13 N6 Nd O13'
_chemical_formula_weight         545.48

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'
Nd Nd -0.1943 3.0179 '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                   16.4141(18)
_cell_length_b                   6.8343(7)
_cell_length_c                   14.5433(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.808(2)
_cell_angle_gamma                90.00
_cell_volume                     1596.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5562
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      26.38

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    2.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1068
_exptl_absorpt_coefficient_mu    3.341
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.713270
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      294(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            8664
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.54
_diffrn_reflns_theta_max         26.40
_reflns_number_total             3257
_reflns_number_gt                2889
_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)+(0.0283P)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         3257
_refine_ls_number_parameters     297
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_ref         0.0521
_refine_ls_wR_factor_gt          0.0500
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.035
_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 0.180868(8) 0.36047(2) 0.794639(9) 0.01490(6) Uani 1 1 d . . .
O1 O 0.32599(13) 0.2492(4) 0.83631(17) 0.0411(6) Uani 1 1 d . . .
O2 O 0.41420(14) 0.2719(4) 0.97396(16) 0.0432(6) Uani 1 1 d . . .
O3 O 0.56675(17) 0.2285(4) 1.03700(18) 0.0470(6) Uani 1 1 d D . .
H3A H 0.5186(15) 0.276(7) 1.018(3) 0.081(17) Uiso 1 1 d D . .
O4 O 0.67745(16) 0.1427(4) 0.9848(2) 0.0513(8) Uani 1 1 d . . .
O5 O 0.03453(11) 0.2585(3) 0.80641(12) 0.0218(4) Uani 1 1 d . . .
O6 O -0.09274(13) 0.1462(3) 0.74953(15) 0.0212(4) Uani 1 1 d . . .
O7 O -0.17390(13) 0.0217(3) 0.56183(14) 0.0284(5) Uani 1 1 d . . .
O8 O -0.16596(14) 0.1671(3) 0.42764(14) 0.0319(5) Uani 1 1 d . . .
O9 O 0.18617(16) 0.0240(3) 0.73701(16) 0.0354(6) Uani 1 1 d D . .
H9A H 0.180(2) -0.016(4) 0.6810(8) 0.054(12) Uiso 1 1 d D . .
H9B H 0.197(2) -0.061(3) 0.7800(13) 0.033(9) Uiso 1 1 d D . .
O10 O 0.23509(14) 0.4505(4) 0.65470(15) 0.0482(7) Uani 1 1 d D . .
H10A H 0.2877 0.4310 0.6648 0.058 Uiso 1 1 d RD . .
H10B H 0.2189 0.5653 0.6342 0.058 Uiso 1 1 d RD . .
O11 O 0.19152(15) 0.1069(3) 0.92536(15) 0.0313(5) Uani 1 1 d D . .
H11A H 0.2377(13) 0.050(6) 0.948(2) 0.059(13) Uiso 1 1 d D . .
H11B H 0.1635(18) 0.141(5) 0.9663(18) 0.047(12) Uiso 1 1 d D . .
O12 O 0.27773(16) 0.6664(4) 0.8221(2) 0.0415(6) Uani 1 1 d D . .
H12A H 0.297(2) 0.704(8) 0.8782(14) 0.090(19) Uiso 1 1 d D . .
H12B H 0.314(2) 0.644(6) 0.789(2) 0.078(18) Uiso 1 1 d D . .
N1 N 0.45369(18) 0.1252(4) 0.7518(2) 0.0310(6) Uani 1 1 d D . .
H1A H 0.4056(14) 0.119(6) 0.710(2) 0.056(13) Uiso 1 1 d D . .
N2 N 0.5253(2) 0.0866(5) 0.7258(2) 0.0422(7) Uani 1 1 d . . .
N3 N 0.58468(18) 0.1015(4) 0.8007(2) 0.0396(7) Uani 1 1 d . . .
N4 N 0.07011(14) 0.2960(3) 0.63485(15) 0.0191(5) Uani 1 1 d . . .
N5 N 0.07333(16) 0.3100(4) 0.54558(16) 0.0235(5) Uani 1 1 d . . .
N6 N -0.00096(15) 0.2537(4) 0.49667(16) 0.0212(5) Uani 1 1 d D . .
H6A H -0.010(2) 0.261(6) 0.4336(8) 0.055(12) Uiso 1 1 d D . .
C1 C 0.39608(18) 0.2343(4) 0.8875(2) 0.0260(7) Uani 1 1 d . . .
C2 C 0.46548(19) 0.1694(4) 0.8433(2) 0.0223(6) Uani 1 1 d . . .
C3 C 0.55015(19) 0.1509(4) 0.8749(2) 0.0261(7) Uani 1 1 d . . .
C4 C 0.6030(2) 0.1743(5) 0.9697(3) 0.0341(8) Uani 1 1 d . . .
C5 C -0.02330(17) 0.2072(4) 0.73999(18) 0.0165(6) Uani 1 1 d . . .
C6 C -0.00621(16) 0.2294(4) 0.64311(18) 0.0166(5) Uani 1 1 d . . .
C7 C -0.05289(18) 0.2004(4) 0.55337(18) 0.0180(6) Uani 1 1 d . . .
C8 C -0.13835(18) 0.1247(4) 0.51128(19) 0.0204(6) Uani 1 1 d . . .
O13 O 0.67543(18) 0.5948(5) 0.89901(17) 0.0487(7) Uani 1 1 d D . .
H13A H 0.718(2) 0.522(7) 0.909(3) 0.11(2) Uiso 1 1 d D . .
H13B H 0.657(3) 0.633(6) 0.9460(19) 0.071(16) Uiso 1 1 d 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 O7 2.3838(19) 2_556 ?
Nd1 O6 2.4370(18) 2_556 ?
Nd1 O9 2.455(2) . ?
Nd1 O1 2.455(2) . ?
Nd1 O10 2.460(2) . ?
Nd1 O5 2.5403(18) . ?
Nd1 O11 2.552(2) . ?
Nd1 O12 2.608(2) . ?
Nd1 N4 2.678(2) . ?
O1 C1 1.240(4) . ?
O2 C1 1.258(4) . ?
O3 C4 1.299(4) . ?
O3 H3A 0.847(10) . ?
O4 C4 1.217(4) . ?
O5 C5 1.258(3) . ?
O6 C5 1.248(3) . ?
O6 Nd1 2.4371(18) 2_546 ?
O7 C8 1.246(3) . ?
O7 Nd1 2.3838(19) 2_546 ?
O8 C8 1.242(3) . ?
O9 H9A 0.845(10) . ?
O9 H9B 0.845(10) . ?
O10 H10A 0.8569 . ?
O10 H10B 0.8625 . ?
O11 H11A 0.857(10) . ?
O11 H11B 0.855(10) . ?
O12 H12A 0.851(10) . ?
O12 H12B 0.849(10) . ?
N1 N2 1.332(4) . ?
N1 C2 1.340(4) . ?
N1 H1A 0.897(10) . ?
N2 N3 1.309(4) . ?
N3 C3 1.360(4) . ?
N4 N5 1.313(3) . ?
N4 C6 1.361(3) . ?
N5 N6 1.336(3) . ?
N6 C7 1.352(3) . ?
N6 H6A 0.899(10) . ?
C1 C2 1.485(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.479(5) . ?
C5 C6 1.499(3) . ?
C6 C7 1.386(4) . ?
C7 C8 1.503(4) . ?
O13 H13A 0.844(10) . ?
O13 H13B 0.845(10) . ?

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
O7 Nd1 O6 74.22(7) 2_556 2_556 ?
O7 Nd1 O9 138.02(7) 2_556 . ?
O6 Nd1 O9 136.15(8) 2_556 . ?
O7 Nd1 O1 98.34(7) 2_556 . ?
O6 Nd1 O1 143.79(8) 2_556 . ?
O9 Nd1 O1 72.17(8) . . ?
O7 Nd1 O10 134.35(9) 2_556 . ?
O6 Nd1 O10 82.95(8) 2_556 . ?
O9 Nd1 O10 84.70(9) . . ?
O1 Nd1 O10 77.57(8) . . ?
O7 Nd1 O5 81.51(7) 2_556 . ?
O6 Nd1 O5 73.69(7) 2_556 . ?
O9 Nd1 O5 82.30(8) . . ?
O1 Nd1 O5 141.38(7) . . ?
O10 Nd1 O5 129.15(7) . . ?
O7 Nd1 O11 70.72(7) 2_556 . ?
O6 Nd1 O11 133.40(7) 2_556 . ?
O9 Nd1 O11 67.45(7) . . ?
O1 Nd1 O11 71.98(8) . . ?
O10 Nd1 O11 143.59(8) . . ?
O5 Nd1 O11 71.64(7) . . ?
O7 Nd1 O12 68.42(9) 2_556 . ?
O6 Nd1 O12 73.03(8) 2_556 . ?
O9 Nd1 O12 137.75(9) . . ?
O1 Nd1 O12 71.35(8) . . ?
O10 Nd1 O12 67.29(9) . . ?
O5 Nd1 O12 139.91(8) . . ?
O11 Nd1 O12 118.93(9) . . ?
O7 Nd1 N4 133.65(7) 2_556 . ?
O6 Nd1 N4 69.03(7) 2_556 . ?
O9 Nd1 N4 67.35(7) . . ?
O1 Nd1 N4 127.97(7) . . ?
O10 Nd1 N4 67.64(7) . . ?
O5 Nd1 N4 61.96(6) . . ?
O11 Nd1 N4 117.75(8) . . ?
O12 Nd1 N4 123.32(8) . . ?
C1 O1 Nd1 155.2(2) . . ?
C4 O3 H3A 113(3) . . ?
C5 O5 Nd1 126.88(16) . . ?
C5 O6 Nd1 138.13(18) . 2_546 ?
C8 O7 Nd1 152.89(19) . 2_546 ?
Nd1 O9 H9A 129(2) . . ?
Nd1 O9 H9B 114.0(19) . . ?
H9A O9 H9B 117.2(18) . . ?
Nd1 O10 H10A 110.0 . . ?
Nd1 O10 H10B 112.1 . . ?
H10A O10 H10B 115.5 . . ?
Nd1 O11 H11A 121(2) . . ?
Nd1 O11 H11B 112(2) . . ?
H11A O11 H11B 114.2(17) . . ?
Nd1 O12 H12A 119(3) . . ?
Nd1 O12 H12B 104(3) . . ?
H12A O12 H12B 116.3(19) . . ?
N2 N1 C2 111.7(3) . . ?
N2 N1 H1A 120(3) . . ?
C2 N1 H1A 128(3) . . ?
N3 N2 N1 107.4(3) . . ?
N2 N3 C3 108.6(3) . . ?
N5 N4 C6 109.6(2) . . ?
N5 N4 Nd1 133.50(17) . . ?
C6 N4 Nd1 116.87(16) . . ?
N4 N5 N6 106.8(2) . . ?
N5 N6 C7 111.9(2) . . ?
N5 N6 H6A 118(3) . . ?
C7 N6 H6A 130(3) . . ?
O1 C1 O2 125.7(3) . . ?
O1 C1 C2 117.7(3) . . ?
O2 C1 C2 116.6(3) . . ?
N1 C2 C3 103.9(3) . . ?
N1 C2 C1 121.9(3) . . ?
C3 C2 C1 134.0(3) . . ?
N3 C3 C2 108.3(3) . . ?
N3 C3 C4 120.4(3) . . ?
C2 C3 C4 131.3(3) . . ?
O4 C4 O3 120.8(3) . . ?
O4 C4 C3 121.7(3) . . ?
O3 C4 C3 117.5(3) . . ?
O6 C5 O5 124.8(2) . . ?
O6 C5 C6 119.3(2) . . ?
O5 C5 C6 115.9(2) . . ?
N4 C6 C7 107.8(2) . . ?
N4 C6 C5 118.0(2) . . ?
C7 C6 C5 134.2(2) . . ?
N6 C7 C6 103.9(2) . . ?
N6 C7 C8 119.8(2) . . ?
C6 C7 C8 136.3(2) . . ?
O8 C8 O7 126.0(3) . . ?
O8 C8 C7 116.2(2) . . ?
O7 C8 C7 117.7(2) . . ?
H13A O13 H13B 118(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 Nd1 O1 C1 -3.6(5) 2_556 . . . ?
O6 Nd1 O1 C1 71.1(5) 2_556 . . . ?
O9 Nd1 O1 C1 -141.5(5) . . . . ?
O10 Nd1 O1 C1 130.2(5) . . . . ?
O5 Nd1 O1 C1 -90.4(5) . . . . ?
O11 Nd1 O1 C1 -70.1(5) . . . . ?
O12 Nd1 O1 C1 60.2(5) . . . . ?
N4 Nd1 O1 C1 178.4(5) . . . . ?
O7 Nd1 O5 C5 156.6(2) 2_556 . . . ?
O6 Nd1 O5 C5 80.7(2) 2_556 . . . ?
O9 Nd1 O5 C5 -62.3(2) . . . . ?
O1 Nd1 O5 C5 -110.6(2) . . . . ?
O10 Nd1 O5 C5 14.4(3) . . . . ?
O11 Nd1 O5 C5 -131.0(2) . . . . ?
O12 Nd1 O5 C5 115.6(2) . . . . ?
N4 Nd1 O5 C5 6.1(2) . . . . ?
C2 N1 N2 N3 1.2(4) . . . . ?
N1 N2 N3 C3 -0.2(4) . . . . ?
O7 Nd1 N4 N5 135.7(2) 2_556 . . . ?
O6 Nd1 N4 N5 95.9(2) 2_556 . . . ?
O9 Nd1 N4 N5 -88.7(2) . . . . ?
O1 Nd1 N4 N5 -47.0(3) . . . . ?
O10 Nd1 N4 N5 5.0(2) . . . . ?
O5 Nd1 N4 N5 178.0(3) . . . . ?
O11 Nd1 N4 N5 -135.1(2) . . . . ?
O12 Nd1 N4 N5 44.6(3) . . . . ?
O7 Nd1 N4 C6 -46.4(2) 2_556 . . . ?
O6 Nd1 N4 C6 -86.26(19) 2_556 . . . ?
O9 Nd1 N4 C6 89.2(2) . . . . ?
O1 Nd1 N4 C6 130.90(19) . . . . ?
O10 Nd1 N4 C6 -177.2(2) . . . . ?
O5 Nd1 N4 C6 -4.11(18) . . . . ?
O11 Nd1 N4 C6 42.8(2) . . . . ?
O12 Nd1 N4 C6 -137.52(19) . . . . ?
C6 N4 N5 N6 0.4(3) . . . . ?
Nd1 N4 N5 N6 178.40(18) . . . . ?
N4 N5 N6 C7 -0.8(3) . . . . ?
Nd1 O1 C1 O2 16.0(8) . . . . ?
Nd1 O1 C1 C2 -162.9(4) . . . . ?
N2 N1 C2 C3 -1.6(3) . . . . ?
N2 N1 C2 C1 174.8(3) . . . . ?
O1 C1 C2 N1 -1.0(4) . . . . ?
O2 C1 C2 N1 180.0(3) . . . . ?
O1 C1 C2 C3 174.2(3) . . . . ?
O2 C1 C2 C3 -4.9(5) . . . . ?
N2 N3 C3 C2 -0.8(4) . . . . ?
N2 N3 C3 C4 178.9(3) . . . . ?
N1 C2 C3 N3 1.5(3) . . . . ?
C1 C2 C3 N3 -174.3(3) . . . . ?
N1 C2 C3 C4 -178.2(3) . . . . ?
C1 C2 C3 C4 6.0(6) . . . . ?
N3 C3 C4 O4 -3.1(5) . . . . ?
C2 C3 C4 O4 176.6(3) . . . . ?
N3 C3 C4 O3 177.6(3) . . . . ?
C2 C3 C4 O3 -2.8(5) . . . . ?
Nd1 O6 C5 O5 -125.1(3) 2_546 . . . ?
Nd1 O6 C5 C6 57.2(4) 2_546 . . . ?
Nd1 O5 C5 O6 175.22(19) . . . . ?
Nd1 O5 C5 C6 -6.9(3) . . . . ?
N5 N4 C6 C7 0.0(3) . . . . ?
Nd1 N4 C6 C7 -178.31(17) . . . . ?
N5 N4 C6 C5 -178.7(2) . . . . ?
Nd1 N4 C6 C5 2.9(3) . . . . ?
O6 C5 C6 N4 -179.9(2) . . . . ?
O5 C5 C6 N4 2.1(4) . . . . ?
O6 C5 C6 C7 1.7(5) . . . . ?
O5 C5 C6 C7 -176.3(3) . . . . ?
N5 N6 C7 C6 0.8(3) . . . . ?
N5 N6 C7 C8 -177.5(2) . . . . ?
N4 C6 C7 N6 -0.5(3) . . . . ?
C5 C6 C7 N6 178.0(3) . . . . ?
N4 C6 C7 C8 177.4(3) . . . . ?
C5 C6 C7 C8 -4.2(6) . . . . ?
Nd1 O7 C8 O8 177.6(3) 2_546 . . . ?
Nd1 O7 C8 C7 -0.2(6) 2_546 . . . ?
N6 C7 C8 O8 -20.2(4) . . . . ?
C6 C7 C8 O8 162.2(3) . . . . ?
N6 C7 C8 O7 157.8(3) . . . . ?
C6 C7 C8 O7 -19.8(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.40
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.016
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.092


_database_code_depnum_ccdc_archive 'CCDC 287165'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Pr_3D
#TrackingRef 'Pr_3D.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H7 N3 O7.50 Pr'
_chemical_formula_sum            'C4 H7 N3 O7.50 Pr'
_chemical_formula_weight         358.04

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'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   P3121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'-x, -x+y, -z+1/3'
'x-y, -y, -z+2/3'

_cell_length_a                   8.8263(12)
_cell_length_b                   8.8263(12)
_cell_length_c                   9.910(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     668.59(19)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             513
_exptl_absorpt_coefficient_mu    5.498
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3520
_exptl_absorpt_correction_T_max  0.6094
_exptl_absorpt_process_details   Crystalclear

_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            6804
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0144
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_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         3.37
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1028
_reflns_number_gt                1027
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Crystalclear
_computing_cell_refinement       Crystalclear
_computing_data_reduction        Crystalclear
_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)+(0.0157P)²+1.0798P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0182(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_number_reflns         1028
_refine_ls_number_parameters     112
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0151
_refine_ls_R_factor_gt           0.0150
_refine_ls_wR_factor_ref         0.0373
_refine_ls_wR_factor_gt          0.0372
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.157
_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
Pr1 Pr 0.77454(2) 1.0000 0.8333 0.00810(9) Uani 1 2 d S . .
C1 C 0.6729(4) 0.7137(4) 0.5623(3) 0.0129(7) Uani 1 1 d . . .
C2 C 0.5266(4) 0.6256(5) 0.6597(3) 0.0127(7) Uani 1 1 d . . .
N1 N 0.9255(4) 0.9255(4) 0.5000 0.0150(8) Uani 1 2 d S . .
N2 N 0.8065(4) 0.8712(4) 0.5986(3) 0.0149(6) Uani 1 1 d . . .
O1 O 0.5340(3) 0.7121(4) 0.7627(3) 0.0205(5) Uani 1 1 d . . .
O2 O 0.4049(3) 0.4717(4) 0.6388(2) 0.0188(5) Uani 1 1 d . . .
O3 O 0.7528(4) 0.7528(4) 1.0000 0.0265(9) Uani 1 2 d S . .
O4 O 0.1881(13) 0.5183(13) 0.8378(10) 0.0623(14) Uani 0.50 1 d PU . .
O5 O 0.261(5) 0.413(6) 0.907(4) 0.0624(14) Uani 0.13 1 d PU . .
O6 O 0.170(3) 0.570(3) 0.780(2) 0.0619(15) Uani 0.25 1 d PU . .
O7 O 0.229(6) 0.453(5) 0.890(4) 0.0621(15) Uani 0.13 1 d PU . .
O8 O 0.405(3) 0.405(3) 1.0000 0.0630(14) Uani 0.25 2 d SPU . .
O9 O 0.120(5) 0.588(5) 0.717(4) 0.0620(15) Uani 0.13 1 d PU . .


_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
Pr1 O2 2.384(2) 2_665 ?
Pr1 O2 2.384(2) 5_666 ?
Pr1 O1 2.462(3) 6_676 ?
Pr1 O1 2.462(3) . ?
Pr1 N1 2.648(4) 2_765 ?
Pr1 N2 2.665(3) 6_676 ?
Pr1 N2 2.665(3) . ?
Pr1 O3 2.6659(17) . ?
Pr1 O3 2.6660(18) 3_674 ?
C1 N2 1.346(4) . ?
C1 C1 1.384(6) 4_556 ?
C1 C2 1.483(5) . ?
C2 O1 1.257(4) . ?
C2 O2 1.258(5) . ?
N1 N2 1.336(3) 4_556 ?
N1 N2 1.336(3) . ?
N1 Pr1 2.648(4) 3_674 ?
O2 Pr1 2.384(2) 3_564 ?
O3 Pr1 2.6659(17) 2_765 ?
O4 O6 0.797(19) . ?
O4 O7 0.97(4) . ?
O4 O5 1.53(4) . ?
O4 O9 1.60(4) . ?
O5 O7 0.58(5) . ?
O5 O8 1.60(4) . ?
O6 O9 0.83(4) . ?
O6 O7 1.75(4) . ?
O8 O9 1.20(4) 6_666 ?
O8 O9 1.20(4) 2_665 ?
O8 O5 1.60(4) 4_557 ?
O9 O8 1.20(4) 3_564 ?

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 Pr1 O2 75.98(12) 2_665 5_666 ?
O2 Pr1 O1 75.82(10) 2_665 6_676 ?
O2 Pr1 O1 72.52(9) 5_666 6_676 ?
O2 Pr1 O1 72.52(9) 2_665 . ?
O2 Pr1 O1 75.81(10) 5_666 . ?
O1 Pr1 O1 139.51(14) 6_676 . ?
O2 Pr1 N1 142.01(6) 2_665 2_765 ?
O2 Pr1 N1 142.01(6) 5_666 2_765 ?
O1 Pr1 N1 110.25(7) 6_676 2_765 ?
O1 Pr1 N1 110.25(7) . 2_765 ?
O2 Pr1 N2 80.06(9) 2_665 6_676 ?
O2 Pr1 N2 132.52(9) 5_666 6_676 ?
O1 Pr1 N2 62.10(9) 6_676 6_676 ?
O1 Pr1 N2 133.55(10) . 6_676 ?
N1 Pr1 N2 71.38(6) 2_765 6_676 ?
O2 Pr1 N2 132.52(9) 2_665 . ?
O2 Pr1 N2 80.05(9) 5_666 . ?
O1 Pr1 N2 133.54(10) 6_676 . ?
O1 Pr1 N2 62.10(9) . . ?
N1 Pr1 N2 71.38(6) 2_765 . ?
N2 Pr1 N2 142.77(13) 6_676 . ?
O2 Pr1 O3 75.90(7) 2_665 . ?
O2 Pr1 O3 140.82(10) 5_666 . ?
O1 Pr1 O3 125.05(7) 6_676 . ?
O1 Pr1 O3 70.07(10) . . ?
N1 Pr1 O3 70.29(6) 2_765 . ?
N2 Pr1 O3 67.27(8) 6_676 . ?
N2 Pr1 O3 99.85(7) . . ?
O2 Pr1 O3 140.82(9) 2_665 3_674 ?
O2 Pr1 O3 75.90(7) 5_666 3_674 ?
O1 Pr1 O3 70.07(10) 6_676 3_674 ?
O1 Pr1 O3 125.05(7) . 3_674 ?
N1 Pr1 O3 70.29(6) 2_765 3_674 ?
N2 Pr1 O3 99.85(7) 6_676 3_674 ?
N2 Pr1 O3 67.27(9) . 3_674 ?
O3 Pr1 O3 140.59(11) . 3_674 ?
N2 C1 C1 107.43(18) . 4_556 ?
N2 C1 C2 116.8(3) . . ?
C1 C1 C2 135.72(19) 4_556 . ?
O1 C2 O2 123.1(3) . . ?
O1 C2 C1 116.3(3) . . ?
O2 C2 C1 120.6(3) . . ?
N2 N1 N2 110.2(4) 4_556 . ?
N2 N1 Pr1 124.92(18) 4_556 3_674 ?
N2 N1 Pr1 124.92(18) . 3_674 ?
N1 N2 C1 107.5(3) . . ?
N1 N2 Pr1 135.8(2) . . ?
C1 N2 Pr1 116.7(2) . . ?
C2 O1 Pr1 127.9(2) . . ?
C2 O2 Pr1 154.0(2) . 3_564 ?
Pr1 O3 Pr1 127.12(15) 2_765 . ?
O6 O4 O7 165(3) . . ?
O6 O4 O5 159(2) . . ?
O7 O4 O5 6(4) . . ?
O6 O4 O9 10(2) . . ?
O7 O4 O9 163(3) . . ?
O5 O4 O9 158(2) . . ?
O7 O5 O4 10(6) . . ?
O7 O5 O8 148(9) . . ?
O4 O5 O8 151(3) . . ?
O4 O6 O9 160(5) . . ?
O4 O6 O7 8.1(19) . . ?
O9 O6 O7 159(4) . . ?
O5 O7 O4 164(10) . . ?
O5 O7 O6 157(9) . . ?
O4 O7 O6 6.7(16) . . ?
O9 O8 O9 121(5) 6_666 2_665 ?
O9 O8 O5 120(2) 6_666 . ?
O9 O8 O5 82(2) 2_665 . ?
O9 O8 O5 82(2) 6_666 4_557 ?
O9 O8 O5 120(2) 2_665 4_557 ?
O5 O8 O5 136(4) . 4_557 ?
O6 O9 O8 153(5) . 3_564 ?
O6 O9 O4 10(2) . . ?
O8 O9 O4 147(3) 3_564 . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.665
_refine_diff_density_min         -0.868
_refine_diff_density_rms         0.094


_database_code_depnum_ccdc_archive 'CCDC 789545'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Nd_3D
#TrackingRef 'Nd_3D.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H7 N3 Nd O7.50'
_chemical_formula_sum            'C4 H7 N3 Nd O7.50'
_chemical_formula_weight         361.37

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           trigonal
_symmetry_space_group_name_H-M   P3121

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'-x, -x+y, -z+1/3'
'x-y, -y, -z+2/3'

_cell_length_a                   8.7561(12)
_cell_length_b                   8.7561(12)
_cell_length_c                   9.855(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     654.35(18)
_cell_formula_units_Z            3
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.751
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    5.984
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3277
_exptl_absorpt_correction_T_max  0.5860
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_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            6814
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_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         3.39
_diffrn_reflns_theta_max         27.48
_reflns_number_total             1008
_reflns_number_gt                998
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Crystalclear
_computing_cell_refinement       Crystalclear
_computing_data_reduction        Crystalclear
_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)+(0.0211P)²+1.5501P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?
_refine_ls_hydrogen_treatment    ?
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.152(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(1)
_refine_ls_number_reflns         1008
_refine_ls_number_parameters     116
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0180
_refine_ls_wR_factor_ref         0.0455
_refine_ls_wR_factor_gt          0.0452
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.042
_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
Nd1 Nd 0.77500(3) 1.0000 0.8333 0.00830(14) Uani 1 2 d S . .
O1 O 0.5342(5) 0.7109(5) 0.7650(4) 0.0233(8) Uani 1 1 d . . .
O2 O 0.4031(4) 0.4698(5) 0.6403(3) 0.0200(7) Uani 1 1 d . . .
O3 O 0.7538(6) 0.7538(6) 1.0000 0.0306(14) Uani 1 2 d S . .
N1 N 0.9263(6) 0.9263(6) 0.5000 0.0163(11) Uani 1 2 d S . .
N2 N 0.8066(5) 0.8707(5) 0.5985(4) 0.0148(8) Uani 1 1 d . . .
C1 C 0.6721(6) 0.7128(6) 0.5630(5) 0.0135(9) Uani 1 1 d . . .
C2 C 0.5252(6) 0.6232(7) 0.6611(5) 0.0134(9) Uani 1 1 d . . .
O4 O 0.186(2) 0.527(2) 0.8336(16) 0.081(3) Uani 0.50 1 d PU . .
O5 O 0.241(9) 0.460(10) 0.889(8) 0.078(4) Uani 0.13 1 d PU . .
O6 O 0.157(5) 0.581(5) 0.759(4) 0.078(4) Uani 0.25 1 d PU . .
O7 O 0.242(9) 0.404(10) 0.910(7) 0.079(4) Uani 0.13 1 d PU . .
O8 O 0.373(8) 0.434(8) 0.983(7) 0.079(5) Uani 0.13 1 d PU . .
O9 O 0.108(8) 0.580(9) 0.690(7) 0.077(5) Uani 0.13 1 d PU . .


_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 O2 2.366(3) 5_666 ?
Nd1 O2 2.366(3) 2_665 ?
Nd1 O1 2.443(4) 6_676 ?
Nd1 O1 2.443(4) . ?
Nd1 N1 2.616(5) 2_765 ?
Nd1 O3 2.642(2) . ?
Nd1 O3 2.642(2) 3_674 ?
Nd1 N2 2.651(4) . ?
Nd1 N2 2.651(4) 6_676 ?
O1 C2 1.259(6) . ?
O2 C2 1.246(6) . ?
O2 Nd1 2.366(3) 3_564 ?
O3 Nd1 2.642(2) 2_765 ?
N1 N2 1.330(5) . ?
N1 N2 1.329(5) 4_556 ?
N1 Nd1 2.616(5) 3_674 ?
N2 C1 1.339(6) . ?
C1 C1 1.387(9) 4_556 ?
C1 C2 1.482(6) . ?
O4 O6 0.98(3) . ?
O4 O5 1.07(7) . ?
O4 O7 1.58(8) . ?
O4 O9 1.74(7) . ?
O5 O7 0.54(13) . ?
O5 O8 1.58(9) . ?
O6 O9 0.80(6) . ?
O6 O8 1.54(7) 3_564 ?
O7 O8 1.26(8) . ?
O7 O9 1.78(10) 2_665 ?
O8 O9 0.82(7) 2_665 ?
O8 O8 0.99(10) 4_557 ?
O8 O9 1.43(8) 6_666 ?
O8 O6 1.54(7) 2_665 ?
O9 O8 0.82(7) 3_564 ?
O9 O8 1.43(8) 6_566 ?
O9 O9 1.70(14) 5_556 ?
O9 O7 1.78(10) 3_564 ?

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 Nd1 O2 77.00(16) 5_666 2_665 ?
O2 Nd1 O1 72.50(13) 5_666 6_676 ?
O2 Nd1 O1 76.16(15) 2_665 6_676 ?
O2 Nd1 O1 76.16(15) 5_666 . ?
O2 Nd1 O1 72.50(13) 2_665 . ?
O1 Nd1 O1 139.6(2) 6_676 . ?
O2 Nd1 N1 141.50(8) 5_666 2_765 ?
O2 Nd1 N1 141.50(8) 2_665 2_765 ?
O1 Nd1 N1 110.18(10) 6_676 2_765 ?
O1 Nd1 N1 110.19(10) . 2_765 ?
O2 Nd1 O3 141.15(13) 5_666 . ?
O2 Nd1 O3 75.50(10) 2_665 . ?
O1 Nd1 O3 125.40(10) 6_676 . ?
O1 Nd1 O3 69.74(14) . . ?
N1 Nd1 O3 70.27(8) 2_765 . ?
O2 Nd1 O3 75.52(10) 5_666 3_674 ?
O2 Nd1 O3 141.16(13) 2_665 3_674 ?
O1 Nd1 O3 69.74(14) 6_676 3_674 ?
O1 Nd1 O3 125.41(10) . 3_674 ?
N1 Nd1 O3 70.25(8) 2_765 3_674 ?
O3 Nd1 O3 140.52(16) . 3_674 ?
O2 Nd1 N2 79.49(13) 5_666 . ?
O2 Nd1 N2 132.86(13) 2_665 . ?
O1 Nd1 N2 133.01(13) 6_676 . ?
O1 Nd1 N2 62.44(12) . . ?
N1 Nd1 N2 71.46(9) 2_765 . ?
O3 Nd1 N2 100.01(10) . . ?
O3 Nd1 N2 67.13(12) 3_674 . ?
O2 Nd1 N2 132.85(12) 5_666 6_676 ?
O2 Nd1 N2 79.49(13) 2_665 6_676 ?
O1 Nd1 N2 62.44(12) 6_676 6_676 ?
O1 Nd1 N2 133.01(14) . 6_676 ?
N1 Nd1 N2 71.45(9) 2_765 6_676 ?
O3 Nd1 N2 67.13(12) . 6_676 ?
O3 Nd1 N2 100.00(10) 3_674 6_676 ?
N2 Nd1 N2 142.91(18) . 6_676 ?
C2 O1 Nd1 127.9(3) . . ?
C2 O2 Nd1 153.4(3) . 3_564 ?
Nd1 O3 Nd1 127.4(2) 2_765 . ?
N2 N1 N2 109.5(5) . 4_556 ?
N2 N1 Nd1 125.3(3) . 3_674 ?
N2 N1 Nd1 125.3(3) 4_556 3_674 ?
N1 N2 C1 108.2(4) . . ?
N1 N2 Nd1 135.4(3) . . ?
C1 N2 Nd1 116.3(3) . . ?
N2 C1 C1 107.0(2) . 4_556 ?
N2 C1 C2 117.3(4) . . ?
C1 C1 C2 135.6(3) 4_556 . ?
O2 C2 O1 123.3(4) . . ?
O2 C2 C1 120.9(4) . . ?
O1 C2 C1 115.8(4) . . ?
O6 O4 O5 161(4) . . ?
O6 O4 O7 159(3) . . ?
O5 O4 O7 8(6) . . ?
O6 O4 O9 12(3) . . ?
O5 O4 O9 155(4) . . ?
O7 O4 O9 151(3) . . ?
O7 O5 O4 155(10) . . ?
O7 O5 O8 45(10) . . ?
O4 O5 O8 159(7) . . ?
O9 O6 O4 154(7) . . ?
O9 O6 O8 18(6) . 3_564 ?
O4 O6 O8 165(4) . 3_564 ?
O5 O7 O8 117(10) . . ?
O5 O7 O4 17(10) . . ?
O8 O7 O4 133(6) . . ?
O5 O7 O9 95(10) . 2_665 ?
O8 O7 O9 24(3) . 2_665 ?
O4 O7 O9 111(5) . 2_665 ?
O9 O8 O8 104(9) 2_665 4_557 ?
O9 O8 O7 116(8) 2_665 . ?
O8 O8 O7 140(7) 4_557 . ?
O9 O8 O9 94(10) 2_665 6_666 ?
O8 O8 O9 34(4) 4_557 6_666 ?
O7 O8 O9 140(7) . 6_666 ?
O9 O8 O6 18(6) 2_665 2_665 ?
O8 O8 O6 102(7) 4_557 2_665 ?
O7 O8 O6 114(5) . 2_665 ?
O9 O8 O6 103(6) 6_666 2_665 ?
O9 O8 O5 100(7) 2_665 . ?
O8 O8 O5 156(8) 4_557 . ?
O7 O8 O5 18(6) . . ?
O9 O8 O5 142(6) 6_666 . ?
O6 O8 O5 102(4) 2_665 . ?
O6 O9 O8 144(10) . 3_564 ?
O6 O9 O8 125(7) . 6_566 ?
O8 O9 O8 42(7) 3_564 6_566 ?
O6 O9 O9 133(9) . 5_556 ?
O8 O9 O9 57(7) 3_564 5_556 ?
O8 O9 O9 29(4) 6_566 5_556 ?
O6 O9 O4 14(4) . . ?
O8 O9 O4 154(9) 3_564 . ?
O8 O9 O4 123(5) 6_566 . ?
O9 O9 O4 123(5) 5_556 . ?
O6 O9 O7 128(8) . 3_564 ?
O8 O9 O7 40(6) 3_564 3_564 ?
O8 O9 O7 82(5) 6_566 3_564 ?
O9 O9 O7 93(5) 5_556 3_564 ?
O4 O9 O7 141(5) . 3_564 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.638
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.104
_database_code_depnum_ccdc_archive 'CCDC 789544'
