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

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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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 retrieval see:
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data_compoundII

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Pr_mal_fumarate
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H14 O15 Pr2'
_chemical_formula_sum            'C10 H14 O15 Pr2'
_chemical_formula_weight         656.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pr Pr -0.2180 2.8214 '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'
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'

_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                   8.3066(4)
_cell_length_b                   9.3439(4)
_cell_length_c                   11.7372(5)
_cell_angle_alpha                79.248(2)
_cell_angle_beta                 70.499(2)
_cell_angle_gamma                75.926(2)
_cell_volume                     827.41(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3222
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      25.99

_exptl_crystal_description       rod
_exptl_crystal_colour            'light green'
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    5.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8428
_exptl_absorpt_correction_T_max  0.9433
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12343
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3222
_reflns_number_gt                2903
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0465P)^2^+0.2026P] where P=(Fo^2^+2Fc^2^)/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         3222
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0792
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Pr1 Pr 0.24998(3) 0.02681(2) 0.48702(2) 0.01262(10) Uani 1 1 d . . .
Pr2 Pr 0.45151(3) -0.35755(2) 0.62670(2) 0.01289(10) Uani 1 1 d . . .
O1 O 0.3915(4) 0.0018(3) 0.2619(3) 0.0189(7) Uani 1 1 d . . .
O2 O 0.0745(4) -0.0903(3) 0.4027(3) 0.0170(7) Uani 1 1 d . . .
O3 O 0.1106(4) 0.2311(3) 0.3580(3) 0.0223(7) Uani 1 1 d . . .
O4 O 0.0847(4) 0.0726(3) 0.7178(3) 0.0225(7) Uani 1 1 d . . .
O5 O 0.2398(4) 0.2973(3) 0.5212(3) 0.0232(8) Uani 1 1 d . . .
O6 O 0.4279(4) -0.2249(3) 0.4179(3) 0.0167(7) Uani 1 1 d . . .
O7 O 0.4530(4) -0.0960(3) 0.6034(3) 0.0142(6) Uani 1 1 d D . .
O8 O 0.1578(4) -0.2146(3) 0.6340(3) 0.0159(6) Uani 1 1 d . . .
O9 O 0.3190(4) -0.5052(3) 0.5413(3) 0.0175(7) Uani 1 1 d . . .
O10 O 0.5592(4) -0.6134(3) 0.7053(3) 0.0238(8) Uani 1 1 d . . .
O11 O 0.1919(4) -0.4500(4) 0.7870(3) 0.0213(7) Uani 1 1 d . . .
O12 O 0.4898(5) -0.3181(4) 0.8117(3) 0.0290(8) Uani 1 1 d . . .
O13 O 0.6054(5) -0.2157(4) 0.9137(3) 0.0334(9) Uani 1 1 d . . .
O14 O 0.1724(6) 0.3030(4) 0.9436(4) 0.0606(13) Uani 1 1 d G . .
H14A H 0.2443 0.2847 0.9842 0.091 Uiso 1 1 d G . .
H14B H 0.1216 0.2300 0.9572 0.091 Uiso 1 1 d G . .
O15 O 0.1024(7) 0.8542(4) 0.9358(5) 0.0794(16) Uani 1 1 d G . .
H15A H 0.0660 0.9295 0.8914 0.119 Uiso 1 1 d G . .
H15B H 0.1872 0.7976 0.8915 0.119 Uiso 1 1 d G . .
C1 C 0.4216(5) -0.2585(4) 0.3204(4) 0.0154(9) Uani 1 1 d . . .
C2 C 0.3915(6) -0.1334(4) 0.2216(4) 0.0156(9) Uani 1 1 d . . .
H2 H 0.4895 -0.1495 0.1473 0.019 Uiso 1 1 calc R . .
C3 C -0.2256(6) 0.1262(5) 0.8069(4) 0.0192(10) Uani 1 1 d G . .
H3A H -0.2191 0.0501 0.8747 0.023 Uiso 1 1 calc R . .
H3B H -0.2306 0.2204 0.8327 0.023 Uiso 1 1 calc R . .
C4 C -0.0610(6) 0.0933(4) 0.7019(4) 0.0162(9) Uani 1 1 d G . .
C5 C 0.2107(6) -0.5927(5) 0.5771(4) 0.0166(10) Uani 1 1 d . . .
C6 C 0.0497(6) -0.5585(5) 0.6815(4) 0.0197(10) Uani 1 1 d . . .
H6A H 0.0402 -0.6464 0.7404 0.024 Uiso 1 1 calc R . .
H6B H -0.0506 -0.5366 0.6519 0.024 Uiso 1 1 calc R . .
C7 C 0.0432(6) -0.4288(4) 0.7461(4) 0.0164(9) Uani 1 1 d . . .
H7 H -0.0602 -0.4234 0.8178 0.020 Uiso 1 1 calc R . .
C8 C -0.0285(6) 0.2786(4) 0.3332(4) 0.0140(9) Uani 1 1 d . . .
C9 C 0.5425(6) -0.3174(5) 0.8998(4) 0.0220(10) Uani 1 1 d . . .
C10 C 0.5262(9) -0.4417(6) 1.0000(5) 0.0425(16) Uani 1 1 d . . .
H10 H 0.5568 -0.4333 1.0675 0.051 Uiso 1 1 calc R . .
H1A H 0.378(7) 0.083(6) 0.201(5) 0.035(15) Uiso 1 1 d . . .
H11A H 0.169(10) -0.516(8) 0.844(7) 0.07(2) Uiso 1 1 d . . .
H7A H 0.439(7) -0.074(6) 0.682(2) 0.034(16) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pr1 0.01280(16) 0.00894(14) 0.01603(16) 0.00195(10) -0.00755(11) -0.00006(10)
Pr2 0.01659(16) 0.00795(14) 0.01445(16) 0.00236(10) -0.00842(11) -0.00048(10)
O1 0.0274(18) 0.0112(14) 0.0193(18) 0.0035(13) -0.0110(14) -0.0047(13)
O2 0.0169(16) 0.0172(15) 0.0150(17) 0.0003(12) -0.0053(13) -0.0010(12)
O3 0.0197(17) 0.0193(16) 0.0256(19) 0.0046(14) -0.0097(14) -0.0013(13)
O4 0.0206(17) 0.0232(16) 0.0259(19) -0.0025(14) -0.0136(14) 0.0007(14)
O5 0.0241(18) 0.0179(16) 0.028(2) -0.0065(14) -0.0061(15) -0.0047(13)
O6 0.0195(16) 0.0149(15) 0.0156(17) 0.0025(12) -0.0101(13) 0.0002(12)
O7 0.0181(16) 0.0104(14) 0.0150(17) 0.0005(12) -0.0088(13) -0.0006(12)
O8 0.0154(16) 0.0100(13) 0.0217(17) 0.0024(12) -0.0089(13) -0.0002(12)
O9 0.0208(17) 0.0120(14) 0.0203(18) 0.0021(12) -0.0076(14) -0.0050(13)
O10 0.038(2) 0.0109(15) 0.0216(18) 0.0017(13) -0.0131(15) 0.0000(14)
O11 0.0205(18) 0.0222(17) 0.0204(19) 0.0067(15) -0.0116(15) -0.0022(14)
O12 0.052(2) 0.0214(17) 0.023(2) 0.0089(14) -0.0236(18) -0.0153(16)
O13 0.061(3) 0.0240(17) 0.029(2) 0.0119(15) -0.0310(19) -0.0208(17)
O14 0.064(3) 0.062(3) 0.064(3) 0.034(2) -0.041(3) -0.027(2)
O15 0.066(4) 0.097(4) 0.071(4) 0.001(3) -0.028(3) -0.007(3)
C1 0.012(2) 0.014(2) 0.018(2) -0.0002(17) -0.0044(18) 0.0007(16)
C2 0.019(2) 0.0111(19) 0.013(2) 0.0011(16) -0.0034(18) 0.0014(17)
C3 0.023(2) 0.021(2) 0.012(2) -0.0006(18) -0.0081(19) 0.0003(19)
C4 0.023(2) 0.0071(19) 0.018(2) 0.0024(17) -0.008(2) -0.0022(18)
C5 0.020(2) 0.011(2) 0.019(3) 0.0036(18) -0.0124(19) 0.0008(18)
C6 0.015(2) 0.019(2) 0.022(3) -0.0008(19) -0.0024(19) -0.0049(18)
C7 0.016(2) 0.013(2) 0.018(2) 0.0018(18) -0.0043(19) -0.0014(17)
C8 0.016(2) 0.0115(19) 0.014(2) -0.0016(16) -0.0068(18) 0.0020(17)
C9 0.031(3) 0.015(2) 0.021(3) 0.0054(19) -0.012(2) -0.004(2)
C10 0.081(5) 0.034(3) 0.029(3) 0.019(2) -0.037(3) -0.030(3)

_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 2.458(3) . ?
Pr1 O3 2.509(3) . ?
Pr1 O7 2.530(3) 2_656 ?
Pr1 O1 2.538(3) . ?
Pr1 O2 2.539(3) . ?
Pr1 O2 2.544(3) 2_556 ?
Pr1 O6 2.568(3) . ?
Pr1 O5 2.609(3) . ?
Pr1 O4 2.659(3) . ?
Pr1 O8 2.676(3) . ?
Pr1 C4 2.979(4) . ?
Pr1 Pr2 3.8859(3) . ?
Pr2 O12 2.402(3) . ?
Pr2 O7 2.411(3) . ?
Pr2 O10 2.460(3) . ?
Pr2 O8 2.462(3) . ?
Pr2 O9 2.472(3) . ?
Pr2 O9 2.532(3) 2_646 ?
Pr2 O11 2.555(3) . ?
Pr2 O6 2.579(3) . ?
Pr2 O5 2.696(3) 2_656 ?
Pr2 C5 3.019(5) 2_646 ?
Pr2 Pr2 4.1102(5) 2_646 ?
O1 C2 1.429(5) . ?
O2 C4 1.276(6) 2_556 ?
O2 Pr1 2.544(3) 2_556 ?
O3 C8 1.243(5) . ?
O4 C4 1.249(5) . ?
O5 C5 1.253(5) 1_565 ?
O5 Pr2 2.696(3) 2_656 ?
O6 C1 1.262(5) . ?
O7 Pr1 2.530(3) 2_656 ?
O8 C8 1.268(5) 2_556 ?
O9 C5 1.278(5) . ?
O9 Pr2 2.532(3) 2_646 ?
O10 C1 1.249(5) 2_646 ?
O11 C7 1.428(5) . ?
O12 C9 1.252(6) . ?
O13 C9 1.249(5) . ?
C1 O10 1.249(5) 2_646 ?
C1 C2 1.522(6) . ?
C2 C3 1.507(6) 2_556 ?
C3 C2 1.507(6) 2_556 ?
C3 C4 1.515(6) . ?
C4 O2 1.276(6) 2_556 ?
C5 O5 1.253(5) 1_545 ?
C5 C6 1.495(6) . ?
C5 Pr2 3.019(5) 2_646 ?
C6 C7 1.526(6) . ?
C7 C8 1.534(6) 2_556 ?
C8 O8 1.268(5) 2_556 ?
C8 C7 1.534(6) 2_556 ?
C9 C10 1.486(7) . ?
C10 C10 1.268(10) 2_647 ?

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 O3 157.00(10) . . ?
O7 Pr1 O7 66.65(11) . 2_656 ?
O3 Pr1 O7 94.06(10) . 2_656 ?
O7 Pr1 O1 110.94(10) . . ?
O3 Pr1 O1 68.27(10) . . ?
O7 Pr1 O1 64.81(10) 2_656 . ?
O7 Pr1 O2 128.54(9) . . ?
O3 Pr1 O2 73.52(10) . . ?
O7 Pr1 O2 132.49(10) 2_656 . ?
O1 Pr1 O2 68.05(10) . . ?
O7 Pr1 O2 119.60(10) . 2_556 ?
O3 Pr1 O2 71.46(10) . 2_556 ?
O7 Pr1 O2 151.35(9) 2_656 2_556 ?
O1 Pr1 O2 126.80(11) . 2_556 ?
O2 Pr1 O2 68.25(11) . 2_556 ?
O7 Pr1 O6 66.70(9) . . ?
O3 Pr1 O6 124.84(10) . . ?
O7 Pr1 O6 81.28(9) 2_656 . ?
O1 Pr1 O6 60.11(9) . . ?
O2 Pr1 O6 70.57(10) . . ?
O2 Pr1 O6 127.34(9) 2_556 . ?
O7 Pr1 O5 96.17(10) . . ?
O3 Pr1 O5 63.89(10) . . ?
O7 Pr1 O5 68.59(9) 2_656 . ?
O1 Pr1 O5 108.08(10) . . ?
O2 Pr1 O5 134.32(10) . . ?
O2 Pr1 O5 82.78(10) 2_556 . ?
O6 Pr1 O5 149.55(10) . . ?
O7 Pr1 O4 73.27(10) . . ?
O3 Pr1 O4 107.11(10) . . ?
O7 Pr1 O4 116.36(9) 2_656 . ?
O1 Pr1 O4 175.37(10) . . ?
O2 Pr1 O4 111.11(10) . . ?
O2 Pr1 O4 49.92(10) 2_556 . ?
O6 Pr1 O4 124.22(10) . . ?
O5 Pr1 O4 69.05(10) . . ?
O7 Pr1 O8 66.52(9) . . ?
O3 Pr1 O8 135.41(9) . . ?
O7 Pr1 O8 129.49(9) 2_656 . ?
O1 Pr1 O8 117.57(9) . . ?
O2 Pr1 O8 69.68(9) . . ?
O2 Pr1 O8 72.11(9) 2_556 . ?
O6 Pr1 O8 63.70(9) . . ?
O5 Pr1 O8 134.31(10) . . ?
O4 Pr1 O8 65.53(9) . . ?
O7 Pr1 C4 96.17(11) . . ?
O3 Pr1 C4 89.72(11) . . ?
O7 Pr1 C4 136.95(10) 2_656 . ?
O1 Pr1 C4 151.91(12) . . ?
O2 Pr1 C4 89.61(11) . . ?
O2 Pr1 C4 25.17(12) 2_556 . ?
O6 Pr1 C4 129.65(10) . . ?
O5 Pr1 C4 74.94(10) . . ?
O4 Pr1 C4 24.76(11) . . ?
O8 Pr1 C4 66.06(10) . . ?
O7 Pr1 Pr2 36.63(6) . . ?
O3 Pr1 Pr2 163.95(7) . . ?
O7 Pr1 Pr2 90.92(7) 2_656 . ?
O1 Pr1 Pr2 100.40(7) . . ?
O2 Pr1 Pr2 91.91(7) . . ?
O2 Pr1 Pr2 109.88(7) 2_556 . ?
O6 Pr1 Pr2 41.09(7) . . ?
O5 Pr1 Pr2 131.94(8) . . ?
O4 Pr1 Pr2 84.13(7) . . ?
O8 Pr1 Pr2 38.84(6) . . ?
C4 Pr1 Pr2 97.02(8) . . ?
O12 Pr2 O7 75.47(10) . . ?
O12 Pr2 O10 78.83(11) . . ?
O7 Pr2 O10 149.19(11) . . ?
O12 Pr2 O8 103.95(11) . . ?
O7 Pr2 O8 70.74(9) . . ?
O10 Pr2 O8 132.86(10) . . ?
O12 Pr2 O9 143.49(11) . . ?
O7 Pr2 O9 132.95(10) . . ?
O10 Pr2 O9 77.67(11) . . ?
O8 Pr2 O9 73.46(10) . . ?
O12 Pr2 O9 125.82(12) . 2_646 ?
O7 Pr2 O9 113.76(10) . 2_646 ?
O10 Pr2 O9 69.11(10) . 2_646 ?
O8 Pr2 O9 129.95(10) . 2_646 ?
O9 Pr2 O9 69.57(11) . 2_646 ?
O12 Pr2 O11 78.36(11) . . ?
O7 Pr2 O11 117.36(10) . . ?
O10 Pr2 O11 72.90(11) . . ?
O8 Pr2 O11 62.12(10) . . ?
O9 Pr2 O11 68.23(10) . . ?
O9 Pr2 O11 127.69(10) 2_646 . ?
O12 Pr2 O6 142.57(10) . . ?
O7 Pr2 O6 67.19(9) . . ?
O10 Pr2 O6 135.20(9) . . ?
O8 Pr2 O6 66.57(9) . . ?
O9 Pr2 O6 71.13(10) . . ?
O9 Pr2 O6 70.27(10) 2_646 . ?
O11 Pr2 O6 121.03(10) . . ?
O12 Pr2 O5 96.13(11) . 2_656 ?
O7 Pr2 O5 68.85(9) . 2_656 ?
O10 Pr2 O5 97.62(11) . 2_656 ?
O8 Pr2 O5 128.04(10) . 2_656 ?
O9 Pr2 O5 114.35(10) . 2_656 ?
O9 Pr2 O5 49.15(9) 2_646 2_656 ?
O11 Pr2 O5 169.70(11) . 2_656 ?
O6 Pr2 O5 68.47(10) . 2_656 ?
O12 Pr2 C5 112.99(12) . 2_646 ?
O7 Pr2 C5 90.89(10) . 2_646 ?
O10 Pr2 C5 83.68(11) . 2_646 ?
O8 Pr2 C5 132.90(11) . 2_646 ?
O9 Pr2 C5 91.73(11) . 2_646 ?
O9 Pr2 C5 24.68(10) 2_646 2_646 ?
O11 Pr2 C5 151.68(11) . 2_646 ?
O6 Pr2 C5 66.33(10) . 2_646 ?
O5 Pr2 C5 24.50(10) 2_656 2_646 ?
O12 Pr2 Pr1 106.73(8) . . ?
O7 Pr2 Pr1 37.46(7) . . ?
O10 Pr2 Pr1 173.35(8) . . ?
O8 Pr2 Pr1 42.96(6) . . ?
O9 Pr2 Pr1 95.71(7) . . ?
O9 Pr2 Pr1 109.27(7) 2_646 . ?
O11 Pr2 Pr1 104.33(7) . . ?
O6 Pr2 Pr1 40.87(6) . . ?
O5 Pr2 Pr1 85.53(7) 2_656 . ?
C5 Pr2 Pr1 97.17(8) 2_646 . ?
O12 Pr2 Pr2 147.56(8) . 2_646 ?
O7 Pr2 Pr2 131.15(7) . 2_646 ?
O10 Pr2 Pr2 69.63(7) . 2_646 ?
O8 Pr2 Pr2 102.97(7) . 2_646 ?
O9 Pr2 Pr2 35.27(7) . 2_646 ?
O9 Pr2 Pr2 34.30(7) 2_646 2_646 ?
O11 Pr2 Pr2 98.84(7) . 2_646 ?
O6 Pr2 Pr2 66.26(6) . 2_646 ?
O5 Pr2 Pr2 81.08(6) 2_656 2_646 ?
C5 Pr2 Pr2 57.20(8) 2_646 2_646 ?
Pr1 Pr2 Pr2 105.258(9) . 2_646 ?
C2 O1 Pr1 116.9(2) . . ?
C4 O2 Pr1 136.3(3) 2_556 . ?
C4 O2 Pr1 96.9(3) 2_556 2_556 ?
Pr1 O2 Pr1 111.75(11) . 2_556 ?
C8 O3 Pr1 141.3(3) . . ?
C4 O4 Pr1 92.1(3) . . ?
C5 O5 Pr1 158.7(3) 1_565 . ?
C5 O5 Pr2 92.3(3) 1_565 2_656 ?
Pr1 O5 Pr2 103.89(10) . 2_656 ?
C1 O6 Pr1 117.7(3) . . ?
C1 O6 Pr2 138.1(3) . . ?
Pr1 O6 Pr2 98.04(10) . . ?
Pr2 O7 Pr1 105.91(11) . . ?
Pr2 O7 Pr1 115.46(11) . 2_656 ?
Pr1 O7 Pr1 113.35(11) . 2_656 ?
C8 O8 Pr2 120.9(2) 2_556 . ?
C8 O8 Pr1 136.6(3) 2_556 . ?
Pr2 O8 Pr1 98.20(9) . . ?
C5 O9 Pr2 139.7(3) . . ?
C5 O9 Pr2 99.5(2) . 2_646 ?
Pr2 O9 Pr2 110.43(11) . 2_646 ?
C1 O10 Pr2 137.4(3) 2_646 . ?
C7 O11 Pr2 113.6(3) . . ?
C9 O12 Pr2 166.8(3) . . ?
O10 C1 O6 126.3(4) 2_646 . ?
O10 C1 C2 115.4(4) 2_646 . ?
O6 C1 C2 118.3(4) . . ?
O1 C2 C3 111.4(3) . 2_556 ?
O1 C2 C1 107.2(3) . . ?
C3 C2 C1 112.8(4) 2_556 . ?
C2 C3 C4 114.6(4) 2_556 . ?
O4 C4 O2 121.1(4) . 2_556 ?
O4 C4 C3 120.2(4) . . ?
O2 C4 C3 118.8(4) 2_556 . ?
O4 C4 Pr1 63.1(2) . . ?
O2 C4 Pr1 58.0(2) 2_556 . ?
C3 C4 Pr1 176.7(3) . . ?
O5 C5 O9 118.9(4) 1_545 . ?
O5 C5 C6 121.7(4) 1_545 . ?
O9 C5 C6 119.3(4) . . ?
O5 C5 Pr2 63.2(2) 1_545 2_646 ?
O9 C5 Pr2 55.8(2) . 2_646 ?
C6 C5 Pr2 174.9(3) . 2_646 ?
C5 C6 C7 114.7(4) . . ?
O11 C7 C6 111.7(3) . . ?
O11 C7 C8 108.4(3) . 2_556 ?
C6 C7 C8 113.2(4) . 2_556 ?
O3 C8 O8 126.4(4) . 2_556 ?
O3 C8 C7 116.3(4) . 2_556 ?
O8 C8 C7 117.3(4) 2_556 2_556 ?
O13 C9 O12 124.8(4) . . ?
O13 C9 C10 115.3(4) . . ?
O12 C9 C10 119.9(4) . . ?
C10 C10 C9 124.7(7) 2_647 . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.191
_refine_diff_density_min         -1.476
_refine_diff_density_rms         0.185
_database_code_depnum_ccdc_archive 'CCDC 969256'
#######################################################################
#
#                 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_compoundIIa

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            pr_mal_fumarate_ht
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 O13 Pr2'
_chemical_formula_sum            'C10 H9 O13 Pr2'
_chemical_formula_weight         618.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pr Pr -0.2180 2.8214 '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'
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'

_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                   8.2557(5)
_cell_length_b                   9.3918(6)
_cell_length_c                   11.6162(8)
_cell_angle_alpha                80.241(6)
_cell_angle_beta                 70.487(6)
_cell_angle_gamma                75.339(5)
_cell_volume                     817.73(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2863
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      25.00

_exptl_crystal_description       rod
_exptl_crystal_colour            'light green'
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             582
_exptl_absorpt_coefficient_mu    5.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8416
_exptl_absorpt_correction_T_max  0.9429
_exptl_absorpt_process_details   '(SADABS;Sheldrick, 1996)'

_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  'Bruker Smart CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6046
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0401
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2863
_reflns_number_gt                2522
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0494P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         2863
_refine_ls_number_parameters     234
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0823
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
Pr01 Pr 0.24981(4) 0.52682(3) 0.48600(3) 0.01978(12) Uani 1 1 d . . .
Pr02 Pr 0.45698(4) 0.14539(3) 0.62575(3) 0.02052(12) Uani 1 1 d . . .
O1 O 0.3953(5) 0.4961(4) 0.2566(4) 0.0289(9) Uani 1 1 d . . .
O2 O 0.0756(5) 0.4100(4) 0.4007(4) 0.0253(9) Uani 1 1 d . . .
O3 O -0.0874(5) 0.4154(4) 0.2839(4) 0.0328(10) Uani 1 1 d . . .
O4 O -0.1109(5) 0.2705(4) 0.6422(4) 0.0324(10) Uani 1 1 d . . .
O5 O 0.2337(5) -0.1966(4) 0.5235(4) 0.0353(10) Uani 1 1 d . . .
O6 O 0.4296(5) 0.2740(4) 0.4158(3) 0.0229(8) Uani 1 1 d . . .
O7 O 0.4550(5) 0.4053(4) 0.6039(3) 0.0225(8) Uani 1 1 d D . .
O8 O 0.1555(5) 0.2888(4) 0.6386(4) 0.0262(9) Uani 1 1 d . . .
O9 O 0.3165(5) -0.0033(4) 0.5474(4) 0.0272(9) Uani 1 1 d . . .
O10 O 0.4342(6) 0.1098(4) 0.2962(4) 0.0372(11) Uani 1 1 d . . .
O11 O 0.1899(5) 0.0538(4) 0.7959(4) 0.0363(10) Uani 1 1 d . . .
O12 O 0.4809(7) 0.1812(4) 0.8146(4) 0.0488(13) Uani 1 1 d . . .
O13 O 0.5944(8) 0.2877(5) 0.9172(4) 0.0538(14) Uani 1 1 d . . .
C1 C 0.4204(7) 0.2389(5) 0.3188(5) 0.0214(12) Uani 1 1 d . . .
C2 C 0.3941(7) 0.3610(6) 0.2181(5) 0.0235(12) Uani 1 1 d . . .
H2 H 0.4935 0.3404 0.1437 0.028 Uiso 1 1 calc R . .
C3 C 0.2242(8) 0.3693(7) 0.1885(5) 0.0283(13) Uani 1 1 d . . .
H3A H 0.2162 0.4457 0.1218 0.034 Uiso 1 1 calc R . .
H3B H 0.2303 0.2760 0.1604 0.034 Uiso 1 1 calc R . .
C4 C 0.0594(8) 0.4020(5) 0.2958(5) 0.0243(12) Uani 1 1 d . . .
C5 C 0.2061(7) -0.0883(6) 0.5822(5) 0.0250(13) Uani 1 1 d . . .
C6 C 0.0485(8) -0.0546(6) 0.6909(6) 0.0322(14) Uani 1 1 d . . .
H6A H 0.0471 -0.1404 0.7506 0.039 Uiso 1 1 calc R . .
H6B H -0.0558 -0.0384 0.6653 0.039 Uiso 1 1 calc R . .
C7 C 0.0377(7) 0.0796(6) 0.7535(5) 0.0264(13) Uani 1 1 d . . .
H7 H -0.0677 0.0891 0.8252 0.032 Uiso 1 1 calc R . .
C8 C 0.0267(7) 0.2261(5) 0.6701(5) 0.0221(12) Uani 1 1 d . . .
C9 C 0.5376(9) 0.1841(6) 0.9021(6) 0.0365(15) Uani 1 1 d . . .
C10 C 0.5330(10) 0.0560(7) 0.9988(6) 0.0484(19) Uani 1 1 d . . .
H10 H 0.5805 0.0570 1.0608 0.058 Uiso 1 1 calc R . .
H1A H 0.397(7) 0.563(6) 0.201(5) 0.018(15) Uiso 1 1 d . . .
H7A H 0.422(11) 0.421(8) 0.687(2) 0.08(3) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Pr01 0.01845(19) 0.01873(19) 0.02217(19) 0.00019(13) -0.00809(14) -0.00276(13)
Pr02 0.0254(2) 0.01725(19) 0.01985(19) 0.00131(13) -0.00995(15) -0.00410(13)
O1 0.042(3) 0.023(2) 0.022(2) 0.0047(18) -0.010(2) -0.0105(18)
O2 0.023(2) 0.028(2) 0.022(2) -0.0042(16) -0.0028(17) -0.0043(16)
O3 0.026(2) 0.040(2) 0.036(2) -0.0057(19) -0.016(2) -0.0022(18)
O4 0.028(2) 0.032(2) 0.035(2) 0.0052(19) -0.013(2) -0.0036(18)
O5 0.033(2) 0.032(2) 0.042(3) -0.012(2) -0.006(2) -0.0100(18)
O6 0.028(2) 0.0236(19) 0.016(2) 0.0001(15) -0.0091(17) -0.0006(16)
O7 0.026(2) 0.0216(19) 0.022(2) -0.0013(16) -0.0094(18) -0.0056(16)
O8 0.025(2) 0.0226(19) 0.031(2) -0.0008(17) -0.0103(18) -0.0046(16)
O9 0.025(2) 0.025(2) 0.029(2) -0.0013(17) -0.0028(18) -0.0082(17)
O10 0.056(3) 0.028(2) 0.030(2) -0.0021(18) -0.023(2) 0.000(2)
O11 0.035(2) 0.040(2) 0.035(3) 0.0076(19) -0.019(2) -0.0060(19)
O12 0.097(4) 0.035(2) 0.031(3) 0.009(2) -0.036(3) -0.027(3)
O13 0.100(4) 0.038(3) 0.038(3) 0.013(2) -0.033(3) -0.034(3)
C1 0.022(3) 0.019(3) 0.017(3) 0.000(2) -0.003(2) 0.002(2)
C2 0.026(3) 0.026(3) 0.013(3) 0.003(2) -0.003(2) -0.005(2)
C3 0.033(3) 0.031(3) 0.022(3) -0.001(2) -0.012(3) -0.005(3)
C4 0.034(3) 0.013(3) 0.028(3) 0.001(2) -0.014(3) -0.004(2)
C5 0.026(3) 0.020(3) 0.032(3) -0.002(2) -0.014(3) -0.002(2)
C6 0.023(3) 0.029(3) 0.040(4) 0.002(3) -0.007(3) -0.005(2)
C7 0.022(3) 0.028(3) 0.025(3) 0.004(2) -0.008(3) -0.002(2)
C8 0.025(3) 0.020(3) 0.018(3) -0.006(2) -0.004(2) 0.001(2)
C9 0.059(4) 0.026(3) 0.026(3) 0.001(3) -0.011(3) -0.014(3)
C10 0.082(5) 0.042(4) 0.034(4) 0.014(3) -0.033(4) -0.026(4)

_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
Pr01 O7 2.467(4) . ?
Pr01 O4 2.496(4) 2_566 ?
Pr01 O7 2.509(4) 2_666 ?
Pr01 O2 2.524(4) . ?
Pr01 O2 2.529(4) 2_566 ?
Pr01 O6 2.563(3) . ?
Pr01 O1 2.564(4) . ?
Pr01 O3 2.639(4) 2_566 ?
Pr01 O5 2.669(4) 1_565 ?
Pr01 O8 2.713(4) . ?
Pr01 C4 2.962(6) 2_566 ?
Pr01 Pr02 3.8956(5) . ?
Pr02 O12 2.353(4) . ?
Pr02 O7 2.408(4) . ?
Pr02 O9 2.466(4) . ?
Pr02 O10 2.468(4) 2_656 ?
Pr02 O8 2.481(4) . ?
Pr02 O9 2.541(4) 2_656 ?
Pr02 O6 2.586(3) . ?
Pr02 O11 2.642(4) . ?
Pr02 O5 2.672(4) 2_656 ?
Pr02 C5 3.009(6) 2_656 ?
Pr02 Pr02 4.1030(6) 2_656 ?
O1 C2 1.419(6) . ?
O2 C4 1.287(7) . ?
O2 Pr01 2.529(4) 2_566 ?
O3 C4 1.238(7) . ?
O3 Pr01 2.639(4) 2_566 ?
O4 C8 1.237(7) . ?
O4 Pr01 2.496(4) 2_566 ?
O5 C5 1.252(6) . ?
O5 Pr01 2.669(4) 1_545 ?
O5 Pr02 2.672(4) 2_656 ?
O6 C1 1.256(6) . ?
O7 Pr01 2.509(4) 2_666 ?
O8 C8 1.263(6) . ?
O9 C5 1.282(7) . ?
O9 Pr02 2.541(4) 2_656 ?
O10 C1 1.254(6) . ?
O10 Pr02 2.468(4) 2_656 ?
O11 C7 1.448(7) . ?
O12 C9 1.259(7) . ?
O13 C9 1.242(7) . ?
C1 C2 1.523(7) . ?
C2 C3 1.532(8) . ?
C3 C4 1.512(8) . ?
C4 Pr01 2.962(6) 2_566 ?
C5 C6 1.488(8) . ?
C5 Pr02 3.009(6) 2_656 ?
C6 C7 1.529(8) . ?
C7 C8 1.544(7) . ?
C9 C10 1.500(8) . ?
C10 C10 1.294(12) 2_657 ?

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 Pr01 O4 156.39(13) . 2_566 ?
O7 Pr01 O7 67.04(14) . 2_666 ?
O4 Pr01 O7 93.18(12) 2_566 2_666 ?
O7 Pr01 O2 128.51(12) . . ?
O4 Pr01 O2 74.21(13) 2_566 . ?
O7 Pr01 O2 132.71(12) 2_666 . ?
O7 Pr01 O2 118.70(12) . 2_566 ?
O4 Pr01 O2 72.57(13) 2_566 2_566 ?
O7 Pr01 O2 151.27(12) 2_666 2_566 ?
O2 Pr01 O2 68.38(14) . 2_566 ?
O7 Pr01 O6 66.87(11) . . ?
O4 Pr01 O6 125.25(12) 2_566 . ?
O7 Pr01 O6 82.13(12) 2_666 . ?
O2 Pr01 O6 70.30(12) . . ?
O2 Pr01 O6 126.53(12) 2_566 . ?
O7 Pr01 O1 110.98(13) . . ?
O4 Pr01 O1 68.55(13) 2_566 . ?
O7 Pr01 O1 65.02(12) 2_666 . ?
O2 Pr01 O1 67.98(12) . . ?
O2 Pr01 O1 127.42(13) 2_566 . ?
O6 Pr01 O1 60.12(11) . . ?
O7 Pr01 O3 73.06(12) . 2_566 ?
O4 Pr01 O3 106.26(13) 2_566 2_566 ?
O7 Pr01 O3 114.61(12) 2_666 2_566 ?
O2 Pr01 O3 112.68(12) . 2_566 ?
O2 Pr01 O3 50.21(12) 2_566 2_566 ?
O6 Pr01 O3 125.30(12) . 2_566 ?
O1 Pr01 O3 174.58(12) . 2_566 ?
O7 Pr01 O5 96.42(12) . 1_565 ?
O4 Pr01 O5 63.10(13) 2_566 1_565 ?
O7 Pr01 O5 68.59(12) 2_666 1_565 ?
O2 Pr01 O5 134.00(13) . 1_565 ?
O2 Pr01 O5 82.69(12) 2_566 1_565 ?
O6 Pr01 O5 150.37(12) . 1_565 ?
O1 Pr01 O5 108.50(13) . 1_565 ?
O3 Pr01 O5 66.97(13) 2_566 1_565 ?
O7 Pr01 O8 66.12(11) . . ?
O4 Pr01 O8 136.15(12) 2_566 . ?
O7 Pr01 O8 129.99(11) 2_666 . ?
O2 Pr01 O8 70.40(11) . . ?
O2 Pr01 O8 70.88(12) 2_566 . ?
O6 Pr01 O8 64.24(11) . . ?
O1 Pr01 O8 118.40(12) . . ?
O3 Pr01 O8 66.28(12) 2_566 . ?
O5 Pr01 O8 133.06(12) 1_565 . ?
O7 Pr01 C4 95.18(14) . 2_566 ?
O4 Pr01 C4 90.40(14) 2_566 2_566 ?
O7 Pr01 C4 135.83(13) 2_666 2_566 ?
O2 Pr01 C4 90.49(14) . 2_566 ?
O2 Pr01 C4 25.57(14) 2_566 2_566 ?
O6 Pr01 C4 129.38(13) . 2_566 ?
O1 Pr01 C4 152.89(14) . 2_566 ?
O3 Pr01 C4 24.67(13) 2_566 2_566 ?
O5 Pr01 C4 74.14(13) 1_565 2_566 ?
O8 Pr01 C4 65.22(12) . 2_566 ?
O7 Pr01 Pr02 36.44(8) . . ?
O4 Pr01 Pr02 164.68(10) 2_566 . ?
O7 Pr01 Pr02 91.23(8) 2_666 . ?
O2 Pr01 Pr02 92.07(8) . . ?
O2 Pr01 Pr02 109.15(9) 2_566 . ?
O6 Pr01 Pr02 41.07(8) . . ?
O1 Pr01 Pr02 100.29(9) . . ?
O3 Pr01 Pr02 85.10(8) 2_566 . ?
O5 Pr01 Pr02 131.97(9) 1_565 . ?
O8 Pr01 Pr02 39.19(8) . . ?
C4 Pr01 Pr02 96.63(10) 2_566 . ?
O12 Pr02 O7 77.29(13) . . ?
O12 Pr02 O9 138.50(14) . . ?
O7 Pr02 O9 133.46(12) . . ?
O12 Pr02 O10 78.13(13) . 2_656 ?
O7 Pr02 O10 149.76(13) . 2_656 ?
O9 Pr02 O10 76.73(13) . 2_656 ?
O12 Pr02 O8 101.46(15) . . ?
O7 Pr02 O8 70.83(12) . . ?
O9 Pr02 O8 72.80(12) . . ?
O10 Pr02 O8 131.74(14) 2_656 . ?
O12 Pr02 O9 129.13(16) . 2_656 ?
O7 Pr02 O9 114.51(12) . 2_656 ?
O9 Pr02 O9 69.93(14) . 2_656 ?
O10 Pr02 O9 69.55(13) 2_656 2_656 ?
O8 Pr02 O9 129.39(13) . 2_656 ?
O12 Pr02 O6 144.63(12) . . ?
O7 Pr02 O6 67.34(12) . . ?
O9 Pr02 O6 72.43(12) . . ?
O10 Pr02 O6 135.10(12) 2_656 . ?
O8 Pr02 O6 67.27(12) . . ?
O9 Pr02 O6 69.63(12) 2_656 . ?
O12 Pr02 O11 74.26(15) . . ?
O7 Pr02 O11 117.07(13) . . ?
O9 Pr02 O11 66.85(13) . . ?
O10 Pr02 O11 72.09(14) 2_656 . ?
O8 Pr02 O11 61.87(12) . . ?
O9 Pr02 O11 127.10(12) 2_656 . ?
O6 Pr02 O11 121.57(12) . . ?
O12 Pr02 O5 99.69(16) . 2_656 ?
O7 Pr02 O5 69.97(12) . 2_656 ?
O9 Pr02 O5 115.80(13) . 2_656 ?
O10 Pr02 O5 97.30(14) 2_656 2_656 ?
O8 Pr02 O5 129.47(13) . 2_656 ?
O9 Pr02 O5 49.44(12) 2_656 2_656 ?
O6 Pr02 O5 68.96(13) . 2_656 ?
O11 Pr02 O5 168.53(13) . 2_656 ?
O12 Pr02 C5 116.69(17) . 2_656 ?
O7 Pr02 C5 91.74(14) . 2_656 ?
O9 Pr02 C5 92.76(14) . 2_656 ?
O10 Pr02 C5 83.80(15) 2_656 2_656 ?
O8 Pr02 C5 133.48(13) . 2_656 ?
O9 Pr02 C5 24.92(13) 2_656 2_656 ?
O6 Pr02 C5 66.20(12) . 2_656 ?
O11 Pr02 C5 151.15(13) . 2_656 ?
O5 Pr02 C5 24.55(13) 2_656 2_656 ?
O12 Pr02 Pr01 107.65(10) . . ?
O7 Pr02 Pr01 37.49(9) . . ?
O9 Pr02 Pr01 96.03(9) . . ?
O10 Pr02 Pr01 172.75(10) 2_656 . ?
O8 Pr02 Pr01 43.71(9) . . ?
O9 Pr02 Pr01 108.61(9) 2_656 . ?
O6 Pr02 Pr01 40.62(8) . . ?
O11 Pr02 Pr01 104.88(8) . . ?
O5 Pr02 Pr01 86.16(9) 2_656 . ?
C5 Pr02 Pr01 97.10(10) 2_656 . ?
O12 Pr02 Pr02 147.23(10) . 2_656 ?
O7 Pr02 Pr02 132.09(9) . 2_656 ?
O9 Pr02 Pr02 35.57(9) . 2_656 ?
O10 Pr02 Pr02 69.25(9) 2_656 2_656 ?
O8 Pr02 Pr02 102.43(9) . 2_656 ?
O9 Pr02 Pr02 34.36(9) 2_656 2_656 ?
O6 Pr02 Pr02 66.62(8) . 2_656 ?
O11 Pr02 Pr02 97.89(9) . 2_656 ?
O5 Pr02 Pr02 81.88(9) 2_656 2_656 ?
C5 Pr02 Pr02 57.81(10) 2_656 2_656 ?
Pr01 Pr02 Pr02 105.113(12) . 2_656 ?
C2 O1 Pr01 115.8(3) . . ?
C4 O2 Pr01 138.1(4) . . ?
C4 O2 Pr01 96.4(3) . 2_566 ?
Pr01 O2 Pr01 111.62(14) . 2_566 ?
C4 O3 Pr01 92.4(3) . 2_566 ?
C8 O4 Pr01 140.7(4) . 2_566 ?
C5 O5 Pr01 158.0(4) . 1_545 ?
C5 O5 Pr02 93.0(3) . 2_656 ?
Pr01 O5 Pr02 102.45(14) 1_545 2_656 ?
C1 O6 Pr01 117.2(3) . . ?
C1 O6 Pr02 138.0(3) . . ?
Pr01 O6 Pr02 98.32(12) . . ?
Pr02 O7 Pr01 106.07(14) . . ?
Pr02 O7 Pr01 115.75(14) . 2_666 ?
Pr01 O7 Pr01 112.96(14) . 2_666 ?
C8 O8 Pr02 121.3(3) . . ?
C8 O8 Pr01 136.1(3) . . ?
Pr02 O8 Pr01 97.10(13) . . ?
C5 O9 Pr02 142.5(4) . . ?
C5 O9 Pr02 98.4(3) . 2_656 ?
Pr02 O9 Pr02 110.07(14) . 2_656 ?
C1 O10 Pr02 138.1(3) . 2_656 ?
C7 O11 Pr02 111.7(3) . . ?
C9 O12 Pr02 164.1(5) . . ?
O10 C1 O6 125.3(5) . . ?
O10 C1 C2 116.2(5) . . ?
O6 C1 C2 118.5(5) . . ?
O1 C2 C1 107.8(4) . . ?
O1 C2 C3 111.5(4) . . ?
C1 C2 C3 112.1(5) . . ?
C4 C3 C2 113.9(5) . . ?
O3 C4 O2 120.8(5) . . ?
O3 C4 C3 120.7(5) . . ?
O2 C4 C3 118.4(5) . . ?
O3 C4 Pr01 62.9(3) . 2_566 ?
O2 C4 Pr01 58.1(3) . 2_566 ?
C3 C4 Pr01 176.2(4) . 2_566 ?
O5 C5 O9 119.0(5) . . ?
O5 C5 C6 122.0(5) . . ?
O9 C5 C6 119.0(5) . . ?
O5 C5 Pr02 62.5(3) . 2_656 ?
O9 C5 Pr02 56.6(3) . 2_656 ?
C6 C5 Pr02 174.7(4) . 2_656 ?
C5 C6 C7 115.1(5) . . ?
O11 C7 C6 108.8(4) . . ?
O11 C7 C8 109.6(4) . . ?
C6 C7 C8 113.6(5) . . ?
O4 C8 O8 126.8(5) . . ?
O4 C8 C7 115.4(5) . . ?
O8 C8 C7 117.8(4) . . ?
O13 C9 O12 125.0(5) . . ?
O13 C9 C10 116.1(5) . . ?
O12 C9 C10 118.8(5) . . ?
C10 C10 C9 123.8(8) 2_657 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.409
_refine_diff_density_min         -1.699
_refine_diff_density_rms         0.181
_database_code_depnum_ccdc_archive 'CCDC 969257'
#######################################################################
#
#                 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_CompoundIII

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Nd_mal_fumarate
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 Nd2 O15'
_chemical_formula_sum            'C10 H10 Nd2 O15'
_chemical_formula_weight         658.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
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'

_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                   8.2494(4)
_cell_length_b                   9.3110(4)
_cell_length_c                   11.6959(6)
_cell_angle_alpha                79.306(4)
_cell_angle_beta                 70.324(4)
_cell_angle_gamma                76.048(4)
_cell_volume                     815.58(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3211
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.00

_exptl_crystal_description       ROD
_exptl_crystal_colour            'Light purple'
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             620
_exptl_absorpt_coefficient_mu    6.378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8830
_exptl_absorpt_correction_T_max  0.9390
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_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  'Bruker Smart CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6081
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3211
_reflns_number_gt                2882
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'

_refine_special_details          
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F^2^, conventional R-factors R are based
 on F, with F set to zero for negative F^2^. The threshold expression of
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0289P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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         3211
_refine_ls_number_parameters     256
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.204
_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
Nd01 Nd 0.74918(3) 0.47453(3) 0.51334(2) 0.00845(9) Uani 1 1 d D . .
Nd02 Nd 0.54904(3) 0.85677(3) 0.37435(2) 0.00879(9) Uani 1 1 d D . .
O1 O 0.6063(5) 0.4998(4) 0.7386(3) 0.0134(8) Uani 1 1 d D . .
O2 O 0.9262(4) 0.5902(4) 0.5970(3) 0.0115(7) Uani 1 1 d . . .
O3 O 1.1140(4) 0.7301(4) 0.3559(3) 0.0150(8) Uani 1 1 d . . .
O4 O 1.0873(4) 0.5703(4) 0.7179(3) 0.0157(8) Uani 1 1 d . . .
O5 O 0.7597(4) 1.2047(4) 0.4792(3) 0.0154(8) Uani 1 1 d . . .
O6 O 0.5718(4) 0.7262(4) 0.5825(3) 0.0107(7) Uani 1 1 d . . .
O7 O 0.5467(4) 0.5961(4) 0.3970(3) 0.0112(7) Uani 1 1 d D . .
O8 O 0.8424(4) 0.7139(4) 0.3670(3) 0.0117(7) Uani 1 1 d . . .
O9 O 0.6809(4) 1.0056(4) 0.4586(3) 0.0110(7) Uani 1 1 d . . .
O10 O 0.5598(5) 0.8900(4) 0.7050(3) 0.0158(8) Uani 1 1 d . . .
O11 O 0.8082(5) 0.9499(4) 0.2129(3) 0.0162(8) Uani 1 1 d D . .
O12 O 0.5150(5) 0.8155(4) 0.1891(3) 0.0198(9) Uani 1 1 d . . .
O13 O 0.3932(5) 0.7162(4) 0.0866(3) 0.0228(9) Uani 1 1 d . . .
O14 O 0.1055(6) 0.3537(6) 0.9353(5) 0.0499(14) Uani 1 1 d . . .
O15 O 0.8299(6) 1.1983(5) 0.0553(4) 0.0400(12) Uani 1 1 d . . .
C1 C 0.5749(6) 0.7622(6) 0.6791(4) 0.0105(11) Uani 1 1 d D . .
C2 C 0.6072(6) 0.6341(6) 0.7788(4) 0.0107(10) Uani 1 1 d . . .
H2 H 0.5085 0.6497 0.8536 0.013 Uiso 1 1 calc R . .
C3 C 0.7747(6) 0.6263(6) 0.8084(5) 0.0145(11) Uani 1 1 d . . .
H3A H 0.7797 0.5505 0.8769 0.017 Uiso 1 1 calc R . .
H3B H 0.7705 0.7209 0.8337 0.017 Uiso 1 1 calc R . .
C4 C 0.9431(6) 0.5910(5) 0.7018(5) 0.0114(11) Uani 1 1 d D . .
C5 C 0.7895(6) 1.0936(6) 0.4236(5) 0.0120(11) Uani 1 1 d . . .
C6 C 0.9531(6) 1.0592(6) 0.3173(5) 0.0135(11) Uani 1 1 d . . .
H6A H 1.0543 1.0379 0.3466 0.016 Uiso 1 1 calc R . .
H6B H 0.9622 1.1472 0.2581 0.016 Uiso 1 1 calc R . .
C7 C 0.9599(6) 0.9283(6) 0.2528(5) 0.0123(11) Uani 1 1 d . . .
H7 H 1.0638 0.9225 0.1804 0.015 Uiso 1 1 calc R . .
C8 C 0.9733(6) 0.7785(6) 0.3335(5) 0.0118(11) Uani 1 1 d . . .
C9 C 0.4575(7) 0.8164(6) 0.1024(5) 0.0177(12) Uani 1 1 d . . .
C10 C 0.4700(11) 0.9434(8) 0.0031(8) 0.056(2) Uani 1 1 d . . .
H10 H 0.4290 0.9377 -0.0606 0.067 Uiso 1 1 calc R . .
H11A H 0.818(9) 1.040(4) 0.160(5) 0.05(2) Uiso 1 1 d D . .
H1A H 0.621(8) 0.421(5) 0.801(4) 0.032(18) Uiso 1 1 d D . .
H7A H 0.551(9) 0.556(8) 0.327(4) 0.05(2) Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Nd01 0.00758(15) 0.00632(15) 0.01220(16) -0.00005(10) -0.00477(11) -0.00099(10)
Nd02 0.01057(15) 0.00606(15) 0.01065(16) 0.00030(10) -0.00526(11) -0.00134(11)
O1 0.0214(19) 0.0074(19) 0.014(2) 0.0014(14) -0.0099(16) -0.0042(15)
O2 0.0122(17) 0.0124(19) 0.0106(19) -0.0009(14) -0.0052(14) -0.0013(14)
O3 0.0127(18) 0.0112(19) 0.021(2) 0.0020(15) -0.0075(16) -0.0026(14)
O4 0.0115(18) 0.017(2) 0.021(2) -0.0036(15) -0.0105(16) 0.0016(15)
O5 0.0124(18) 0.014(2) 0.023(2) -0.0078(16) -0.0055(16) -0.0026(15)
O6 0.0129(17) 0.0088(19) 0.0103(18) -0.0012(14) -0.0043(14) -0.0008(14)
O7 0.0112(17) 0.0106(19) 0.0110(18) -0.0015(14) -0.0023(15) -0.0020(14)
O8 0.0095(17) 0.0097(19) 0.0158(19) -0.0012(14) -0.0049(15) -0.0005(14)
O9 0.0112(17) 0.0101(19) 0.0116(18) -0.0006(14) -0.0017(14) -0.0047(14)
O10 0.024(2) 0.0078(19) 0.014(2) 0.0007(14) -0.0089(16) 0.0013(15)
O11 0.0148(18) 0.018(2) 0.017(2) 0.0043(16) -0.0090(16) -0.0035(16)
O12 0.033(2) 0.016(2) 0.017(2) 0.0025(15) -0.0146(18) -0.0106(17)
O13 0.038(2) 0.017(2) 0.020(2) 0.0029(16) -0.0161(19) -0.0124(18)
O14 0.047(3) 0.059(4) 0.044(3) -0.002(3) -0.017(3) -0.009(3)
O15 0.043(3) 0.036(3) 0.044(3) 0.019(2) -0.025(2) -0.015(2)
C1 0.007(2) 0.011(3) 0.009(3) -0.001(2) 0.002(2) 0.0003(19)
C2 0.014(3) 0.012(3) 0.006(2) -0.0004(19) -0.005(2) 0.000(2)
C3 0.015(3) 0.018(3) 0.011(3) -0.003(2) -0.006(2) -0.002(2)
C4 0.014(3) 0.002(2) 0.017(3) 0.0004(19) -0.005(2) -0.0008(19)
C5 0.011(2) 0.009(3) 0.015(3) -0.001(2) -0.007(2) 0.004(2)
C6 0.010(2) 0.014(3) 0.017(3) 0.000(2) -0.004(2) -0.004(2)
C7 0.010(2) 0.014(3) 0.013(3) 0.001(2) -0.004(2) -0.003(2)
C8 0.009(2) 0.013(3) 0.012(3) -0.004(2) -0.002(2) 0.001(2)
C9 0.023(3) 0.013(3) 0.017(3) 0.004(2) -0.009(2) -0.006(2)
C10 0.090(6) 0.045(5) 0.062(6) 0.037(4) -0.061(5) -0.046(4)

_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
Nd01 O7 2.443(4) . ?
Nd01 O7 2.507(3) 2_666 ?
Nd01 O3 2.507(4) 2_766 ?
Nd01 O2 2.522(4) . ?
Nd01 O2 2.526(3) 2_766 ?
Nd01 O1 2.528(4) . ?
Nd01 O6 2.557(3) . ?
Nd01 O5 2.593(4) 1_545 ?
Nd01 O4 2.646(4) 2_766 ?
Nd01 O8 2.648(3) . ?
Nd01 C4 2.944(5) 2_766 ?
Nd01 Nd02 3.8551(4) . ?
Nd02 O12 2.385(4) . ?
Nd02 O7 2.396(3) . ?
Nd02 O10 2.440(3) 2_676 ?
Nd02 O8 2.446(3) . ?
Nd02 O9 2.455(3) . ?
Nd02 O9 2.514(3) 2_676 ?
Nd02 O11 2.541(3) . ?
Nd02 O6 2.557(3) . ?
Nd02 O5 2.674(3) 2_676 ?
Nd02 C5 2.989(5) 2_676 ?
Nd02 Nd02 4.0835(6) 2_676 ?
O1 C2 1.418(6) . ?
O2 C4 1.280(6) . ?
O2 Nd01 2.526(3) 2_766 ?
O3 C8 1.236(6) . ?
O3 Nd01 2.507(4) 2_766 ?
O4 C4 1.230(6) . ?
O4 Nd01 2.646(4) 2_766 ?
O5 C5 1.254(6) . ?
O5 Nd01 2.593(4) 1_565 ?
O5 Nd02 2.674(3) 2_676 ?
O6 C1 1.247(6) . ?
O7 Nd01 2.507(3) 2_666 ?
O8 C8 1.274(6) . ?
O9 C5 1.274(6) . ?
O9 Nd02 2.514(3) 2_676 ?
O10 C1 1.249(6) . ?
O10 Nd02 2.440(3) 2_676 ?
O11 C7 1.435(6) . ?
O12 C9 1.255(7) . ?
O13 C9 1.247(6) . ?
C1 C2 1.547(7) . ?
C2 C3 1.516(7) . ?
C3 C4 1.536(7) . ?
C4 Nd01 2.944(5) 2_766 ?
C5 C6 1.510(7) . ?
C5 Nd02 2.989(5) 2_676 ?
C6 C7 1.528(7) . ?
C7 C8 1.535(7) . ?
C9 C10 1.492(8) . ?
C10 C10 1.249(14) 2_675 ?

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 Nd01 O7 66.73(13) . 2_666 ?
O7 Nd01 O3 156.61(11) . 2_766 ?
O7 Nd01 O3 93.39(11) 2_666 2_766 ?
O7 Nd01 O2 128.94(11) . . ?
O7 Nd01 O2 132.98(11) 2_666 . ?
O3 Nd01 O2 73.46(11) 2_766 . ?
O7 Nd01 O2 119.55(11) . 2_766 ?
O7 Nd01 O2 150.58(11) 2_666 2_766 ?
O3 Nd01 O2 71.83(11) 2_766 2_766 ?
O2 Nd01 O2 68.25(13) . 2_766 ?
O7 Nd01 O1 110.99(11) . . ?
O7 Nd01 O1 65.01(11) 2_666 . ?
O3 Nd01 O1 67.89(12) 2_766 . ?
O2 Nd01 O1 68.25(11) . . ?
O2 Nd01 O1 126.96(11) 2_766 . ?
O7 Nd01 O6 66.93(11) . . ?
O7 Nd01 O6 81.86(11) 2_666 . ?
O3 Nd01 O6 124.55(11) 2_766 . ?
O2 Nd01 O6 70.77(11) . . ?
O2 Nd01 O6 127.53(11) 2_766 . ?
O1 Nd01 O6 60.13(11) . . ?
O7 Nd01 O5 96.12(11) . 1_545 ?
O7 Nd01 O5 68.28(11) 2_666 1_545 ?
O3 Nd01 O5 63.79(12) 2_766 1_545 ?
O2 Nd01 O5 133.90(11) . 1_545 ?
O2 Nd01 O5 82.31(11) 2_766 1_545 ?
O1 Nd01 O5 108.10(11) . 1_545 ?
O6 Nd01 O5 149.83(11) . 1_545 ?
O7 Nd01 O4 72.63(11) . 2_766 ?
O7 Nd01 O4 115.68(11) 2_666 2_766 ?
O3 Nd01 O4 107.97(11) 2_766 2_766 ?
O2 Nd01 O4 111.31(11) . 2_766 ?
O2 Nd01 O4 50.32(11) 2_766 2_766 ?
O1 Nd01 O4 175.85(11) . 2_766 ?
O6 Nd01 O4 123.86(11) . 2_766 ?
O5 Nd01 O4 69.06(11) 1_545 2_766 ?
O7 Nd01 O8 66.61(11) . . ?
O7 Nd01 O8 129.81(11) 2_666 . ?
O3 Nd01 O8 135.79(11) 2_766 . ?
O2 Nd01 O8 69.80(11) . . ?
O2 Nd01 O8 72.31(10) 2_766 . ?
O1 Nd01 O8 117.64(11) . . ?
O6 Nd01 O8 63.66(10) . . ?
O5 Nd01 O8 134.22(11) 1_545 . ?
O4 Nd01 O8 65.37(11) 2_766 . ?
O7 Nd01 C4 95.52(13) . 2_766 ?
O7 Nd01 C4 136.16(13) 2_666 2_766 ?
O3 Nd01 C4 90.66(13) 2_766 2_766 ?
O2 Nd01 C4 89.87(12) . 2_766 ?
O2 Nd01 C4 25.64(13) 2_766 2_766 ?
O1 Nd01 C4 152.56(13) . 2_766 ?
O6 Nd01 C4 129.45(12) . 2_766 ?
O5 Nd01 C4 74.72(12) 1_545 2_766 ?
O4 Nd01 C4 24.69(12) 2_766 2_766 ?
O8 Nd01 C4 65.86(12) . 2_766 ?
O7 Nd01 Nd02 36.77(8) . . ?
O7 Nd01 Nd02 91.21(8) 2_666 . ?
O3 Nd01 Nd02 163.89(9) 2_766 . ?
O2 Nd01 Nd02 92.17(8) . . ?
O2 Nd01 Nd02 110.10(8) 2_766 . ?
O1 Nd01 Nd02 100.38(8) . . ?
O6 Nd01 Nd02 41.08(8) . . ?
O5 Nd01 Nd02 132.03(8) 1_545 . ?
O4 Nd01 Nd02 83.74(8) 2_766 . ?
O8 Nd01 Nd02 38.89(7) . . ?
C4 Nd01 Nd02 96.67(9) 2_766 . ?
O12 Nd02 O7 75.04(12) . . ?
O12 Nd02 O10 78.72(13) . 2_676 ?
O7 Nd02 O10 148.35(12) . 2_676 ?
O12 Nd02 O8 103.20(13) . . ?
O7 Nd02 O8 70.69(11) . . ?
O10 Nd02 O8 133.43(12) 2_676 . ?
O12 Nd02 O9 143.05(12) . . ?
O7 Nd02 O9 133.51(12) . . ?
O10 Nd02 O9 77.95(12) 2_676 . ?
O8 Nd02 O9 73.85(11) . . ?
O12 Nd02 O9 126.43(13) . 2_676 ?
O7 Nd02 O9 114.01(11) . 2_676 ?
O10 Nd02 O9 69.06(11) 2_676 2_676 ?
O8 Nd02 O9 130.11(12) . 2_676 ?
O9 Nd02 O9 69.48(12) . 2_676 ?
O12 Nd02 O11 77.56(12) . . ?
O7 Nd02 O11 117.45(12) . . ?
O10 Nd02 O11 72.80(12) 2_676 . ?
O8 Nd02 O11 62.66(11) . . ?
O9 Nd02 O11 68.37(11) . . ?
O9 Nd02 O11 127.52(11) 2_676 . ?
O12 Nd02 O6 142.59(12) . . ?
O7 Nd02 O6 67.61(11) . . ?
O10 Nd02 O6 135.42(11) 2_676 . ?
O8 Nd02 O6 66.55(11) . . ?
O9 Nd02 O6 71.25(11) . . ?
O9 Nd02 O6 70.34(11) 2_676 . ?
O11 Nd02 O6 121.42(11) . . ?
O12 Nd02 O5 96.28(12) . 2_676 ?
O7 Nd02 O5 68.50(11) . 2_676 ?
O10 Nd02 O5 97.49(12) 2_676 2_676 ?
O8 Nd02 O5 127.82(11) . 2_676 ?
O9 Nd02 O5 114.85(11) . 2_676 ?
O9 Nd02 O5 49.69(11) 2_676 2_676 ?
O11 Nd02 O5 169.26(11) . 2_676 ?
O6 Nd02 O5 68.69(11) . 2_676 ?
O12 Nd02 C5 113.36(14) . 2_676 ?
O7 Nd02 C5 90.92(12) . 2_676 ?
O10 Nd02 C5 83.47(12) 2_676 2_676 ?
O8 Nd02 C5 133.09(13) . 2_676 ?
O9 Nd02 C5 91.95(13) . 2_676 ?
O9 Nd02 C5 24.91(13) 2_676 2_676 ?
O11 Nd02 C5 151.61(13) . 2_676 ?
O6 Nd02 C5 66.55(12) . 2_676 ?
O5 Nd02 C5 24.80(12) 2_676 2_676 ?
O12 Nd02 Nd01 106.24(9) . . ?
O7 Nd02 Nd01 37.61(9) . . ?
O10 Nd02 Nd01 174.03(9) 2_676 . ?
O8 Nd02 Nd01 42.83(8) . . ?
O9 Nd02 Nd01 96.10(8) . . ?
O9 Nd02 Nd01 109.50(8) 2_676 . ?
O11 Nd02 Nd01 104.71(8) . . ?
O6 Nd02 Nd01 41.07(7) . . ?
O5 Nd02 Nd01 85.39(8) 2_676 . ?
C5 Nd02 Nd01 97.33(9) 2_676 . ?
O12 Nd02 Nd02 147.78(9) . 2_676 ?
O7 Nd02 Nd02 131.64(9) . 2_676 ?
O10 Nd02 Nd02 69.78(9) 2_676 2_676 ?
O8 Nd02 Nd02 103.27(8) . 2_676 ?
O9 Nd02 Nd02 35.21(8) . 2_676 ?
O9 Nd02 Nd02 34.26(8) 2_676 2_676 ?
O11 Nd02 Nd02 98.83(9) . 2_676 ?
O6 Nd02 Nd02 66.40(8) . 2_676 ?
O5 Nd02 Nd02 81.62(8) 2_676 2_676 ?
C5 Nd02 Nd02 57.45(10) 2_676 2_676 ?
Nd01 Nd02 Nd02 105.626(11) . 2_676 ?
C2 O1 Nd01 116.9(3) . . ?
C4 O2 Nd01 136.5(3) . . ?
C4 O2 Nd01 95.7(3) . 2_766 ?
Nd01 O2 Nd01 111.75(13) . 2_766 ?
C8 O3 Nd01 140.5(3) . 2_766 ?
C4 O4 Nd01 91.4(3) . 2_766 ?
C5 O5 Nd01 159.1(3) . 1_565 ?
C5 O5 Nd02 91.8(3) . 2_676 ?
Nd01 O5 Nd02 104.19(12) 1_565 2_676 ?
C1 O6 Nd01 119.1(3) . . ?
C1 O6 Nd02 137.3(3) . . ?
Nd01 O6 Nd02 97.85(11) . . ?
Nd02 O7 Nd01 105.62(13) . . ?
Nd02 O7 Nd01 115.90(13) . 2_666 ?
Nd01 O7 Nd01 113.27(13) . 2_666 ?
C8 O8 Nd02 120.7(3) . . ?
C8 O8 Nd01 136.7(3) . . ?
Nd02 O8 Nd01 98.28(11) . . ?
C5 O9 Nd02 140.5(3) . . ?
C5 O9 Nd02 98.9(3) . 2_676 ?
Nd02 O9 Nd02 110.52(12) . 2_676 ?
C1 O10 Nd02 135.8(3) . 2_676 ?
C7 O11 Nd02 113.7(3) . . ?
C9 O12 Nd02 164.4(4) . . ?
O6 C1 O10 128.0(5) . . ?
O6 C1 C2 116.9(4) . . ?
O10 C1 C2 115.1(4) . . ?
O1 C2 C3 111.7(4) . . ?
O1 C2 C1 107.3(4) . . ?
C3 C2 C1 113.6(4) . . ?
C2 C3 C4 114.2(4) . . ?
O4 C4 O2 122.5(5) . . ?
O4 C4 C3 120.0(5) . . ?
O2 C4 C3 117.5(4) . . ?
O4 C4 Nd01 63.9(3) . 2_766 ?
O2 C4 Nd01 58.6(2) . 2_766 ?
C3 C4 Nd01 176.1(4) . 2_766 ?
O5 C5 O9 119.5(4) . . ?
O5 C5 C6 121.7(4) . . ?
O9 C5 C6 118.8(5) . . ?
O5 C5 Nd02 63.4(3) . 2_676 ?
O9 C5 Nd02 56.2(2) . 2_676 ?
C6 C5 Nd02 174.6(4) . 2_676 ?
C5 C6 C7 114.7(4) . . ?
O11 C7 C6 111.2(4) . . ?
O11 C7 C8 108.3(4) . . ?
C6 C7 C8 112.9(4) . . ?
O3 C8 O8 126.4(5) . . ?
O3 C8 C7 116.1(4) . . ?
O8 C8 C7 117.4(4) . . ?
O13 C9 O12 126.2(5) . . ?
O13 C9 C10 114.0(5) . . ?
O12 C9 C10 119.8(5) . . ?
C10 C10 C9 126.5(9) 2_675 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.953
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.157
_database_code_depnum_ccdc_archive 'CCDC 969258'