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

#######################################################################
#
#                 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.
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data_sa1473
#TrackingRef 'Nd(NO3)3+Picolinamide.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H24 N11 Nd O13'
_chemical_formula_weight         818.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

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

_cell_length_a                   10.180(2)
_cell_length_b                   11.926(2)
_cell_length_c                   13.693(3)
_cell_angle_alpha                105.79(3)
_cell_angle_beta                 97.96(3)
_cell_angle_gamma                95.69(3)
_cell_volume                     1567.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6098
_cell_measurement_theta_min      1.5691
_cell_measurement_theta_max      27.4847

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             818
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7524
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13994
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7130
_reflns_number_gt                6770
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0677P)²+1.1602P] 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         7130
_refine_ls_number_parameters     442
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.214
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Nd1 Nd 0.229798(18) 0.287732(16) 0.632668(14) 0.01652(9) Uani 1 1 d . . .
O1 O 0.2893(3) 0.3034(3) 0.4684(2) 0.0234(6) Uani 1 1 d . . .
O2 O 0.1032(3) 0.4532(2) 0.6676(2) 0.0201(6) Uani 1 1 d . . .
O3 O 0.3242(3) 0.1834(3) 0.7487(2) 0.0245(6) Uani 1 1 d . . .
O4 O 0.3891(3) 0.4856(3) 0.6568(2) 0.0225(6) Uani 1 1 d . . .
O5 O 0.4880(3) 0.3340(3) 0.6588(3) 0.0298(7) Uani 1 1 d . . .
O6 O 0.6061(3) 0.5017(3) 0.6733(3) 0.0404(9) Uani 1 1 d . . .
O7 O 0.0368(3) 0.2438(3) 0.7224(2) 0.0236(6) Uani 1 1 d . . .
O8 O 0.0747(3) 0.0923(3) 0.6065(2) 0.0245(6) Uani 1 1 d . . .
O9 O -0.0641(3) 0.0693(3) 0.7092(3) 0.0335(7) Uani 1 1 d . . .
O10 O 0.0225(4) 0.4231(3) 0.1031(2) 0.0315(7) Uani 1 1 d . . .
O11 O 0.5016(5) 0.2275(4) 0.1298(3) 0.0495(10) Uani 1 1 d . . .
O12 O 0.5517(4) 0.0896(3) 0.1960(3) 0.0322(7) Uani 1 1 d . . .
O13 O 0.6238(8) 0.1097(7) 0.0624(5) 0.121(3) Uani 1 1 d U . .
N1 N 0.3038(3) 0.0999(3) 0.5085(3) 0.0220(7) Uani 1 1 d . . .
N2 N 0.4011(4) 0.2547(3) 0.3352(3) 0.0279(8) Uani 1 1 d . . .
H2B H 0.4038 0.3242 0.3277 0.033 Uiso 1 1 calc R . .
H2A H 0.4366 0.2019 0.2952 0.033 Uiso 1 1 calc R . .
N3 N 0.0053(3) 0.2757(3) 0.4990(3) 0.0207(7) Uani 1 1 d . . .
N4 N -0.1036(4) 0.4993(4) 0.6844(3) 0.0289(8) Uani 1 1 d . . .
H4B H -0.0756 0.5458 0.7455 0.035 Uiso 1 1 calc R . .
H4A H -0.1869 0.4898 0.6574 0.035 Uiso 1 1 calc R . .
N5 N 0.3035(3) 0.4086(3) 0.8321(3) 0.0199(7) Uani 1 1 d . . .
N6 N 0.4332(4) 0.1653(3) 0.8968(3) 0.0270(8) Uani 1 1 d . . .
H6B H 0.4497 0.0961 0.8667 0.032 Uiso 1 1 calc R . .
H6A H 0.4606 0.1960 0.9619 0.032 Uiso 1 1 calc R . .
N7 N 0.4955(3) 0.4415(3) 0.6625(3) 0.0241(7) Uani 1 1 d . . .
N8 N 0.0131(3) 0.1327(3) 0.6800(3) 0.0206(7) Uani 1 1 d . . .
N9 N 0.1204(4) 0.1597(3) -0.0386(3) 0.0291(8) Uani 1 1 d . . .
N10 N 0.0054(4) 0.3448(3) -0.0683(3) 0.0295(8) Uani 1 1 d . . .
H10B H -0.0203 0.4069 -0.0806 0.035 Uiso 1 1 calc R . .
H10A H 0.0135 0.2856 -0.1184 0.035 Uiso 1 1 calc R . .
N11 N 0.5595(4) 0.1423(4) 0.1284(3) 0.0328(9) Uani 1 1 d . . .
C1 C 0.3017(4) -0.0059(4) 0.5270(4) 0.0271(9) Uani 1 1 d . . .
H1 H 0.2776 -0.0131 0.5883 0.032 Uiso 1 1 calc R . .
C2 C 0.3338(5) -0.1039(4) 0.4589(4) 0.0282(9) Uani 1 1 d . . .
H2 H 0.3307 -0.1754 0.4742 0.034 Uiso 1 1 calc R . .
C3 C 0.3703(5) -0.0945(4) 0.3680(4) 0.0307(10) Uani 1 1 d . . .
H3 H 0.3918 -0.1596 0.3210 0.037 Uiso 1 1 calc R . .
C4 C 0.3747(4) 0.0140(4) 0.3475(4) 0.0260(9) Uani 1 1 d . . .
H4 H 0.3993 0.0231 0.2868 0.031 Uiso 1 1 calc R . .
C5 C 0.3413(4) 0.1086(4) 0.4205(3) 0.0211(8) Uani 1 1 d . . .
C6 C 0.3427(4) 0.2293(4) 0.4080(3) 0.0199(8) Uani 1 1 d . . .
C7 C -0.0341(4) 0.1964(4) 0.4067(3) 0.0239(8) Uani 1 1 d . . .
H7 H 0.0151 0.1349 0.3874 0.029 Uiso 1 1 calc R . .
C8 C -0.1461(5) 0.2024(4) 0.3381(3) 0.0298(10) Uani 1 1 d . . .
H8 H -0.1703 0.1463 0.2741 0.036 Uiso 1 1 calc R . .
C9 C -0.2209(4) 0.2932(4) 0.3665(3) 0.0272(9) Uani 1 1 d . . .
H9 H -0.2947 0.3001 0.3213 0.033 Uiso 1 1 calc R . .
C10 C -0.1840(4) 0.3727(4) 0.4627(3) 0.0232(8) Uani 1 1 d . . .
H10 H -0.2339 0.4332 0.4845 0.028 Uiso 1 1 calc R . .
C11 C -0.0719(4) 0.3612(4) 0.5265(3) 0.0201(8) Uani 1 1 d . . .
C12 C -0.0186(4) 0.4424(4) 0.6319(3) 0.0196(8) Uani 1 1 d . . .
C13 C 0.2833(4) 0.5195(4) 0.8742(3) 0.0246(9) Uani 1 1 d . . .
H13 H 0.2569 0.5635 0.8303 0.029 Uiso 1 1 calc R . .
C14 C 0.2994(4) 0.5724(4) 0.9796(4) 0.0270(9) Uani 1 1 d . . .
H14 H 0.2862 0.6503 1.0054 0.032 Uiso 1 1 calc R . .
C15 C 0.3356(4) 0.5067(4) 1.0453(3) 0.0272(9) Uani 1 1 d . . .
H15 H 0.3435 0.5387 1.1162 0.033 Uiso 1 1 calc R . .
C16 C 0.3601(4) 0.3923(4) 1.0043(3) 0.0256(9) Uani 1 1 d . . .
H16 H 0.3871 0.3471 1.0471 0.031 Uiso 1 1 calc R . .
C17 C 0.3435(4) 0.3468(4) 0.8980(3) 0.0202(8) Uani 1 1 d . . .
C18 C 0.3659(4) 0.2243(4) 0.8431(3) 0.0204(8) Uani 1 1 d . . .
C19 C 0.1680(5) 0.0633(4) -0.0249(4) 0.0366(11) Uani 1 1 d . . .
H19 H 0.1993 0.0148 -0.0797 0.044 Uiso 1 1 calc R . .
C20 C 0.1737(5) 0.0316(5) 0.0639(5) 0.0397(12) Uani 1 1 d . . .
H20 H 0.2072 -0.0369 0.0688 0.048 Uiso 1 1 calc R . .
C21 C 0.1289(6) 0.1030(5) 0.1462(4) 0.0416(13) Uani 1 1 d . . .
H21 H 0.1310 0.0837 0.2078 0.050 Uiso 1 1 calc R . .
C22 C 0.0805(5) 0.2043(4) 0.1347(4) 0.0341(11) Uani 1 1 d . . .
H22 H 0.0497 0.2544 0.1888 0.041 Uiso 1 1 calc R . .
C23 C 0.0786(4) 0.2298(4) 0.0421(3) 0.0256(9) Uani 1 1 d . . .
C24 C 0.0323(4) 0.3403(4) 0.0273(3) 0.0255(9) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O3 2.427(3) . ?
Nd1 O2 2.439(3) . ?
Nd1 O1 2.458(3) . ?
Nd1 O7 2.541(3) . ?
Nd1 O5 2.586(3) . ?
Nd1 O8 2.591(3) . ?
Nd1 O4 2.641(3) . ?
Nd1 N1 2.663(4) . ?
Nd1 N5 2.678(4) . ?
Nd1 N3 2.688(4) . ?
Nd1 N8 2.991(3) . ?
O1 C6 1.258(5) . ?
O2 C12 1.248(5) . ?
O3 C18 1.246(5) . ?
O4 N7 1.251(4) . ?
O5 N7 1.264(5) . ?
O6 N7 1.241(5) . ?
O7 N8 1.278(4) . ?
O8 N8 1.268(5) . ?
O9 N8 1.217(5) . ?
O10 C24 1.246(5) . ?
O11 N11 1.221(5) . ?
O12 N11 1.259(5) . ?
O13 N11 1.191(6) . ?
N1 C5 1.341(5) . ?
N1 C1 1.351(5) . ?
N2 C6 1.316(5) . ?
N2 H2B 0.8600 . ?
N2 H2A 0.8600 . ?
N3 C7 1.337(5) . ?
N3 C11 1.354(5) . ?
N4 C12 1.322(5) . ?
N4 H4B 0.8600 . ?
N4 H4A 0.8600 . ?
N5 C13 1.341(5) . ?
N5 C17 1.358(5) . ?
N6 C18 1.321(5) . ?
N6 H6B 0.8600 . ?
N6 H6A 0.8600 . ?
N9 C23 1.340(6) . ?
N9 C19 1.340(6) . ?
N10 C24 1.316(6) . ?
N10 H10B 0.8600 . ?
N10 H10A 0.8600 . ?
C1 C2 1.382(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.494(6) . ?
C7 C8 1.394(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.385(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.494(6) . ?
C13 C14 1.388(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.507(6) . ?
C19 C20 1.364(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.389(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.498(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Nd1 O2 129.38(10) . . ?
O3 Nd1 O1 130.11(10) . . ?
O2 Nd1 O1 98.06(10) . . ?
O3 Nd1 O7 76.55(10) . . ?
O2 Nd1 O7 69.58(10) . . ?
O1 Nd1 O7 144.42(10) . . ?
O3 Nd1 O5 72.03(11) . . ?
O2 Nd1 O5 117.85(10) . . ?
O1 Nd1 O5 72.44(11) . . ?
O7 Nd1 O5 143.08(10) . . ?
O3 Nd1 O8 70.28(11) . . ?
O2 Nd1 O8 110.26(10) . . ?
O1 Nd1 O8 111.03(10) . . ?
O7 Nd1 O8 49.84(10) . . ?
O5 Nd1 O8 130.86(10) . . ?
O3 Nd1 O4 109.96(10) . . ?
O2 Nd1 O4 70.27(9) . . ?
O1 Nd1 O4 68.18(10) . . ?
O7 Nd1 O4 130.97(10) . . ?
O5 Nd1 O4 48.78(9) . . ?
O8 Nd1 O4 179.16(8) . . ?
O3 Nd1 N1 75.92(10) . . ?
O2 Nd1 N1 153.03(10) . . ?
O1 Nd1 N1 61.99(10) . . ?
O7 Nd1 N1 115.15(10) . . ?
O5 Nd1 N1 75.41(11) . . ?
O8 Nd1 N1 65.76(10) . . ?
O4 Nd1 N1 113.46(10) . . ?
O3 Nd1 N5 62.56(10) . . ?
O2 Nd1 N5 72.14(10) . . ?
O1 Nd1 N5 136.43(10) . . ?
O7 Nd1 N5 73.19(10) . . ?
O5 Nd1 N5 75.40(11) . . ?
O8 Nd1 N5 112.16(10) . . ?
O4 Nd1 N5 68.60(10) . . ?
N1 Nd1 N5 134.76(11) . . ?
O3 Nd1 N3 140.10(11) . . ?
O2 Nd1 N3 62.35(10) . . ?
O1 Nd1 N3 70.54(10) . . ?
O7 Nd1 N3 74.29(10) . . ?
O5 Nd1 N3 142.45(11) . . ?
O8 Nd1 N3 70.17(11) . . ?
O4 Nd1 N3 109.67(10) . . ?
N1 Nd1 N3 92.53(11) . . ?
N5 Nd1 N3 130.79(10) . . ?
O3 Nd1 N8 69.57(10) . . ?
O2 Nd1 N8 91.15(10) . . ?
O1 Nd1 N8 131.71(10) . . ?
O7 Nd1 N8 25.05(9) . . ?
O5 Nd1 N8 141.23(10) . . ?
O8 Nd1 N8 24.96(10) . . ?
O4 Nd1 N8 155.87(10) . . ?
N1 Nd1 N8 90.14(10) . . ?
N5 Nd1 N8 91.52(10) . . ?
N3 Nd1 N8 72.46(10) . . ?
C6 O1 Nd1 125.8(3) . . ?
C12 O2 Nd1 121.9(3) . . ?
C18 O3 Nd1 127.1(3) . . ?
N7 O4 Nd1 95.3(2) . . ?
N7 O5 Nd1 97.6(2) . . ?
N8 O7 Nd1 97.6(2) . . ?
N8 O8 Nd1 95.5(2) . . ?
C5 N1 C1 117.4(4) . . ?
C5 N1 Nd1 118.6(3) . . ?
C1 N1 Nd1 124.0(3) . . ?
C6 N2 H2B 120.0 . . ?
C6 N2 H2A 120.0 . . ?
H2B N2 H2A 120.0 . . ?
C7 N3 C11 117.2(4) . . ?
C7 N3 Nd1 126.3(3) . . ?
C11 N3 Nd1 116.5(3) . . ?
C12 N4 H4B 120.0 . . ?
C12 N4 H4A 120.0 . . ?
H4B N4 H4A 120.0 . . ?
C13 N5 C17 116.8(4) . . ?
C13 N5 Nd1 125.2(3) . . ?
C17 N5 Nd1 117.0(3) . . ?
C18 N6 H6B 120.0 . . ?
C18 N6 H6A 120.0 . . ?
H6B N6 H6A 120.0 . . ?
O6 N7 O4 121.3(4) . . ?
O6 N7 O5 120.4(4) . . ?
O4 N7 O5 118.3(3) . . ?
O9 N8 O8 122.1(4) . . ?
O9 N8 O7 121.5(4) . . ?
O8 N8 O7 116.4(3) . . ?
O9 N8 Nd1 172.2(3) . . ?
O8 N8 Nd1 59.58(19) . . ?
O7 N8 Nd1 57.38(18) . . ?
C23 N9 C19 116.8(4) . . ?
C24 N10 H10B 120.0 . . ?
C24 N10 H10A 120.0 . . ?
H10B N10 H10A 120.0 . . ?
O13 N11 O11 119.3(5) . . ?
O13 N11 O12 120.3(5) . . ?
O11 N11 O12 120.4(4) . . ?
N1 C1 C2 123.0(4) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.0(4) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 123.3(4) . . ?
N1 C5 C6 113.4(4) . . ?
C4 C5 C6 123.4(4) . . ?
O1 C6 N2 122.4(4) . . ?
O1 C6 C5 118.6(4) . . ?
N2 C6 C5 118.9(4) . . ?
N3 C7 C8 122.6(4) . . ?
N3 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 118.7(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C9 C10 C11 118.9(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
N3 C11 C10 123.4(4) . . ?
N3 C11 C12 111.9(3) . . ?
C10 C11 C12 124.7(4) . . ?
O2 C12 N4 122.5(4) . . ?
O2 C12 C11 119.3(4) . . ?
N4 C12 C11 118.2(4) . . ?
N5 C13 C14 123.8(4) . . ?
N5 C13 H13 118.1 . . ?
C14 C13 H13 118.1 . . ?
C15 C14 C13 118.4(4) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 119.3(4) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 118.5(4) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
N5 C17 C16 123.1(4) . . ?
N5 C17 C18 112.6(3) . . ?
C16 C17 C18 124.2(4) . . ?
O3 C18 N6 122.3(4) . . ?
O3 C18 C17 119.4(3) . . ?
N6 C18 C17 118.3(4) . . ?
N9 C19 C20 124.4(5) . . ?
N9 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
C19 C20 C21 118.7(5) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C22 118.2(5) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C23 C22 C21 119.2(5) . . ?
C23 C22 H22 120.4 . . ?
C21 C22 H22 120.4 . . ?
N9 C23 C22 122.7(4) . . ?
N9 C23 C24 116.1(4) . . ?
C22 C23 C24 121.2(4) . . ?
O10 C24 N10 123.0(4) . . ?
O10 C24 C23 120.4(4) . . ?
N10 C24 C23 116.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.370
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.225


_database_code_depnum_ccdc_archive 'CCDC 841635'
#######################################################################
#
#                 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_mx1358
#TrackingRef 'mx1358.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 La O7,3(Cl)'
_chemical_formula_sum            'C12 H22 Cl3 La N4 O7'
_chemical_formula_weight         579.60

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.898(6)
_cell_length_b                   7.7600(16)
_cell_length_c                   19.778(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.39(3)
_cell_angle_gamma                90.00
_cell_volume                     4296.1(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7210
_cell_measurement_theta_min      1.4550
_cell_measurement_theta_max      27.4851

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2288
_exptl_absorpt_coefficient_mu    2.401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8092
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15489
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.45
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4909
_reflns_number_gt                4444
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0400P)²+18.2173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4909
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_restrained_S_all      1.249
_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
La1 La 0.108158(11) 0.77250(4) 0.206269(16) 0.02089(11) Uani 1 1 d . . .
Cl1 Cl 0.06280(5) 0.2867(2) 0.06827(7) 0.0276(3) Uani 1 1 d . . .
Cl2 Cl 0.06225(5) 0.24776(19) 0.31166(7) 0.0287(3) Uani 1 1 d . . .
Cl3 Cl 0.24949(5) 0.5397(2) 0.14832(8) 0.0325(3) Uani 1 1 d . . .
O2 O 0.06261(14) 0.7516(5) 0.0830(2) 0.0273(9) Uani 1 1 d . . .
O6 O 0.20021(14) 0.7681(5) 0.2411(2) 0.0301(10) Uani 1 1 d . . .
H6A H 0.2187 0.7264 0.2186 0.036 Uiso 1 1 d R . .
H6B H 0.2197 0.8337 0.2677 0.036 Uiso 1 1 d R . .
O3 O 0.04456(13) 1.0082(5) 0.17436(19) 0.0248(9) Uani 1 1 d . . .
H3A H 0.0425 1.0787 0.2057 0.030 Uiso 1 1 d R . .
H3B H 0.0394 1.0456 0.1333 0.030 Uiso 1 1 d R . .
O1 O 0.06183(15) 0.8031(6) 0.2939(2) 0.0291(9) Uani 1 1 d . . .
O5 O 0.04955(14) 0.5279(5) 0.1930(2) 0.0293(9) Uani 1 1 d . . .
H5A H 0.0407 0.4752 0.1548 0.035 Uiso 1 1 d R . .
H5B H 0.0506 0.4506 0.2230 0.035 Uiso 1 1 d R . .
O7 O 0.14399(15) 0.5121(6) 0.1581(2) 0.0417(12) Uani 1 1 d . . .
H7A H 0.1273 0.4417 0.1301 0.050 Uiso 1 1 d R . .
H7B H 0.1635 0.5180 0.1329 0.050 Uiso 1 1 d R . .
O4 O 0.14202(15) 1.0384(6) 0.2751(2) 0.0417(12) Uani 1 1 d . . .
H4A H 0.1218 1.0971 0.2891 0.050 Uiso 1 1 d R . .
H4B H 0.1691 1.0485 0.3029 0.050 Uiso 1 1 d R . .
N3 N 0.14133(17) 0.9395(7) 0.1044(2) 0.0266(11) Uani 1 1 d . . .
N1 N 0.13732(16) 0.6025(6) 0.3297(2) 0.0243(10) Uani 1 1 d . . .
N4 N 0.05181(19) 0.7471(7) -0.0328(3) 0.0354(13) Uani 1 1 d . . .
H4C H 0.0251 0.6883 -0.0384 0.043 Uiso 1 1 calc R . .
H4D H 0.0623 0.7766 -0.0693 0.043 Uiso 1 1 calc R . .
N2 N 0.04457(18) 0.7874(7) 0.3982(3) 0.0300(12) Uani 1 1 d . . .
H2D H 0.0191 0.8528 0.3839 0.036 Uiso 1 1 calc R . .
H2C H 0.0521 0.7476 0.4412 0.036 Uiso 1 1 calc R . .
C6 C 0.0715(2) 0.7490(7) 0.3550(3) 0.0247(12) Uani 1 1 d . . .
C1 C 0.11420(19) 0.6352(7) 0.3798(3) 0.0221(12) Uani 1 1 d . . .
C12 C 0.0761(2) 0.7907(8) 0.0300(3) 0.0264(13) Uani 1 1 d . . .
C7 C 0.1209(2) 0.8953(8) 0.0380(3) 0.0260(12) Uani 1 1 d . . .
C11 C 0.1793(2) 1.0426(8) 0.1163(3) 0.0319(14) Uani 1 1 d . . .
H11 H 0.1938 1.0748 0.1632 0.038 Uiso 1 1 calc R . .
C8 C 0.1390(2) 0.9468(8) -0.0174(3) 0.0284(13) Uani 1 1 d . . .
H8 H 0.1242 0.9111 -0.0637 0.034 Uiso 1 1 calc R . .
C5 C 0.1744(2) 0.4935(8) 0.3455(3) 0.0307(14) Uani 1 1 d . . .
H5 H 0.1899 0.4642 0.3100 0.037 Uiso 1 1 calc R . .
C4 C 0.1910(2) 0.4217(8) 0.4108(3) 0.0300(13) Uani 1 1 d . . .
H4 H 0.2174 0.3446 0.4197 0.036 Uiso 1 1 calc R . .
C2 C 0.1291(2) 0.5707(8) 0.4468(3) 0.0288(13) Uani 1 1 d . . .
H2 H 0.1125 0.5993 0.4812 0.035 Uiso 1 1 calc R . .
C9 C 0.1791(2) 1.0516(9) -0.0041(3) 0.0358(15) Uani 1 1 d . . .
H9 H 0.1929 1.0858 -0.0409 0.043 Uiso 1 1 calc R . .
C3 C 0.1690(2) 0.4630(8) 0.4632(3) 0.0315(14) Uani 1 1 d . . .
H3 H 0.1806 0.4191 0.5091 0.038 Uiso 1 1 calc R . .
C10 C 0.1989(2) 1.1055(8) 0.0636(3) 0.0336(14) Uani 1 1 d . . .
H10 H 0.2250 1.1834 0.0739 0.040 Uiso 1 1 calc 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
La1 O1 2.451(4) . ?
La1 O2 2.472(4) . ?
La1 O5 2.513(4) . ?
La1 O4 2.531(4) . ?
La1 O3 2.558(4) . ?
La1 O7 2.560(4) . ?
La1 O6 2.577(4) . ?
La1 N1 2.718(5) . ?
La1 N3 2.759(5) . ?
O2 C12 1.242(7) . ?
O1 C6 1.243(7) . ?
N3 C11 1.331(8) . ?
N3 C7 1.344(7) . ?
N1 C5 1.339(7) . ?
N1 C1 1.349(6) . ?
N4 C12 1.310(7) . ?
N2 C6 1.324(7) . ?
C6 C1 1.498(8) . ?
C1 C2 1.383(8) . ?
C12 C7 1.503(8) . ?
C7 C8 1.387(7) . ?
C11 C10 1.392(8) . ?
C8 C9 1.387(9) . ?
C5 C4 1.380(8) . ?
C4 C3 1.381(8) . ?
C2 C3 1.395(8) . ?
C9 C10 1.384(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 La1 O2 116.98(13) . . ?
O1 La1 O5 71.04(14) . . ?
O2 La1 O5 70.57(13) . . ?
O1 La1 O4 75.33(15) . . ?
O2 La1 O4 128.60(15) . . ?
O5 La1 O4 146.33(13) . . ?
O1 La1 O3 67.68(13) . . ?
O2 La1 O3 68.26(13) . . ?
O5 La1 O3 95.16(14) . . ?
O4 La1 O3 73.02(13) . . ?
O1 La1 O7 133.04(15) . . ?
O2 La1 O7 75.31(14) . . ?
O5 La1 O7 71.91(13) . . ?
O4 La1 O7 134.88(14) . . ?
O3 La1 O7 143.57(14) . . ?
O1 La1 O6 121.39(14) . . ?
O2 La1 O6 121.62(13) . . ?
O5 La1 O6 129.94(13) . . ?
O4 La1 O6 68.37(13) . . ?
O3 La1 O6 134.91(13) . . ?
O7 La1 O6 66.62(13) . . ?
O1 La1 N1 60.89(13) . . ?
O2 La1 N1 145.55(14) . . ?
O5 La1 N1 77.18(14) . . ?
O4 La1 N1 85.43(15) . . ?
O3 La1 N1 127.73(12) . . ?
O7 La1 N1 83.56(15) . . ?
O6 La1 N1 71.59(14) . . ?
O1 La1 N3 145.15(14) . . ?
O2 La1 N3 60.47(14) . . ?
O5 La1 N3 128.71(14) . . ?
O4 La1 N3 81.47(15) . . ?
O3 La1 N3 80.95(13) . . ?
O7 La1 N3 81.53(15) . . ?
O6 La1 N3 71.26(14) . . ?
N1 La1 N3 142.85(14) . . ?
C12 O2 La1 127.9(4) . . ?
C6 O1 La1 128.6(4) . . ?
C11 N3 C7 118.0(5) . . ?
C11 N3 La1 125.0(4) . . ?
C7 N3 La1 116.4(4) . . ?
C5 N1 C1 117.5(5) . . ?
C5 N1 La1 124.5(4) . . ?
C1 N1 La1 117.9(4) . . ?
O1 C6 N2 121.6(6) . . ?
O1 C6 C1 119.0(5) . . ?
N2 C6 C1 119.4(5) . . ?
N1 C1 C2 122.9(5) . . ?
N1 C1 C6 112.9(5) . . ?
C2 C1 C6 124.2(5) . . ?
O2 C12 N4 122.1(6) . . ?
O2 C12 C7 119.0(5) . . ?
N4 C12 C7 118.9(5) . . ?
N3 C7 C8 122.6(6) . . ?
N3 C7 C12 113.5(5) . . ?
C8 C7 C12 123.9(5) . . ?
N3 C11 C10 123.3(6) . . ?
C9 C8 C7 118.8(6) . . ?
N1 C5 C4 123.1(5) . . ?
C5 C4 C3 119.4(6) . . ?
C1 C2 C3 118.8(5) . . ?
C10 C9 C8 119.0(6) . . ?
C4 C3 C2 118.3(6) . . ?
C9 C10 C11 118.2(6) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.191


_database_code_depnum_ccdc_archive 'CCDC 918184'
#######################################################################
#
#                 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_mx1252
#TrackingRef 'mx1252.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 Nd O7,3(Cl)'
_chemical_formula_sum            'C12 H22 Cl3 N4 Nd O7'
_chemical_formula_weight         584.93

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'
Cl Cl 0.1484 0.1585 '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   C2/c

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

_cell_length_a                   28.770(6)
_cell_length_b                   7.7390(15)
_cell_length_c                   19.629(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.26(3)
_cell_angle_gamma                90.00
_cell_volume                     4235.8(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7253
_cell_measurement_theta_min      1.0704
_cell_measurement_theta_max      27.4816

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2312
_exptl_absorpt_coefficient_mu    2.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8316
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14524
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4833
_reflns_number_gt                4675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0224P)²+6.5470P] 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         4833
_refine_ls_number_parameters     332
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0607
_refine_ls_wR_factor_gt          0.0598
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.134
_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 0.108134(5) 0.727539(17) 0.205955(7) 0.01894(5) Uani 1 1 d . . .
Cl2 Cl 0.06294(2) 0.21195(8) 0.06769(3) 0.02534(14) Uani 1 1 d . . .
Cl3 Cl 0.06264(3) 0.25268(8) 0.31168(4) 0.02622(14) Uani 1 1 d . . .
O2 O 0.06257(7) 0.7536(2) 0.08470(10) 0.0247(4) Uani 1 1 d . . .
O1 O 0.06183(7) 0.6934(2) 0.29168(9) 0.0242(4) Uani 1 1 d . . .
N3 N 0.14054(8) 0.5622(3) 0.10667(12) 0.0251(5) Uani 1 1 d . . .
N2 N 0.04428(9) 0.7090(3) 0.39630(13) 0.0272(5) Uani 1 1 d D . .
N1 N 0.13707(8) 0.8970(3) 0.32674(11) 0.0227(4) Uani 1 1 d . . .
C5 C 0.17423(10) 1.0060(4) 0.34227(15) 0.0272(6) Uani 1 1 d . . .
C12 C 0.07609(10) 0.7131(3) 0.03115(14) 0.0230(5) Uani 1 1 d . . .
N4 N 0.05193(10) 0.7584(4) -0.03209(13) 0.0316(6) Uani 1 1 d D . .
C7 C 0.12066(9) 0.6067(3) 0.03960(13) 0.0221(5) Uani 1 1 d . . .
C1 C 0.11440(9) 0.8628(3) 0.37763(13) 0.0205(5) Uani 1 1 d . . .
C2 C 0.12963(10) 0.9273(4) 0.44530(14) 0.0249(5) Uani 1 1 d . . .
C10 C 0.19853(11) 0.3945(4) 0.06595(16) 0.0312(6) Uani 1 1 d . . .
C6 C 0.07128(10) 0.7480(3) 0.35296(14) 0.0201(5) Uani 1 1 d . . .
C4 C 0.19127(10) 1.0780(4) 0.40833(15) 0.0282(6) Uani 1 1 d . . .
C8 C 0.13925(10) 0.5549(4) -0.01591(15) 0.0270(6) Uani 1 1 d . . .
C11 C 0.17822(10) 0.4556(4) 0.11850(16) 0.0291(6) Uani 1 1 d . . .
C9 C 0.17927(11) 0.4490(4) -0.00240(16) 0.0312(6) Uani 1 1 d . . .
C3 C 0.16961(10) 1.0349(4) 0.46099(15) 0.0285(6) Uani 1 1 d . . .
Cl1 Cl 0.24947(2) 0.96178(9) 0.14845(4) 0.02913(15) Uani 1 1 d . . .
O7 O 0.04592(7) 0.4940(2) 0.17387(10) 0.0231(4) Uani 1 1 d D . .
O6 O 0.05022(7) 0.9666(3) 0.19347(10) 0.0262(4) Uani 1 1 d D . .
O4 O 0.19890(7) 0.7306(3) 0.24053(12) 0.0290(4) Uani 1 1 d D . .
O5 O 0.14315(8) 0.9818(3) 0.15784(13) 0.0363(5) Uani 1 1 d D . .
O3 O 0.14135(8) 0.4680(3) 0.27461(13) 0.0369(5) Uani 1 1 d D . .
H11 H 0.1907(10) 0.420(4) 0.1643(14) 0.016(7) Uiso 1 1 d . . .
H4 H 0.2147(11) 1.162(4) 0.4127(15) 0.023(7) Uiso 1 1 d . . .
H8 H 0.1244(10) 0.583(4) -0.0605(16) 0.022(7) Uiso 1 1 d . . .
H2 H 0.1146(11) 0.895(4) 0.4816(16) 0.029(8) Uiso 1 1 d . . .
H3 H 0.1819(10) 1.081(4) 0.5076(15) 0.023(7) Uiso 1 1 d . . .
H14B H 0.2165(12) 0.771(4) 0.2165(18) 0.040(10) Uiso 1 1 d D . .
H24A H 0.0591(14) 0.735(4) -0.0716(13) 0.042(11) Uiso 1 1 d D . .
H10 H 0.2256(13) 0.311(4) 0.0783(18) 0.037(9) Uiso 1 1 d . . .
H14A H 0.2168(11) 0.676(4) 0.2734(14) 0.037(9) Uiso 1 1 d D . .
H9 H 0.1913(13) 0.415(5) -0.043(2) 0.054(11) Uiso 1 1 d . . .
H22B H 0.0517(14) 0.749(4) 0.4400(11) 0.043(11) Uiso 1 1 d D . .
H24B H 0.0241(9) 0.809(4) -0.0352(18) 0.040(10) Uiso 1 1 d D . .
H17A H 0.0422(14) 0.441(4) 0.2077(14) 0.051(12) Uiso 1 1 d D . .
H17B H 0.0472(13) 0.417(4) 0.1459(16) 0.046(11) Uiso 1 1 d D . .
H22A H 0.0177(9) 0.650(4) 0.3804(18) 0.047(10) Uiso 1 1 d D . .
H13A H 0.1676(9) 0.449(5) 0.3021(17) 0.056(12) Uiso 1 1 d D . .
H5 H 0.1912(11) 1.022(4) 0.3068(16) 0.034(9) Uiso 1 1 d . . .
H13B H 0.1223(12) 0.405(5) 0.288(2) 0.064(13) Uiso 1 1 d D . .
H16A H 0.0447(11) 1.027(3) 0.1582(12) 0.024(8) Uiso 1 1 d D . .
H16B H 0.0523(12) 1.030(4) 0.2276(13) 0.039(10) Uiso 1 1 d D . .
H15B H 0.1238(10) 1.050(4) 0.1332(16) 0.038(10) Uiso 1 1 d D . .
H15A H 0.1696(9) 0.998(5) 0.149(2) 0.065(13) 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 O1 2.4043(19) . ?
Nd1 O2 2.426(2) . ?
Nd1 O6 2.4614(19) . ?
Nd1 O3 2.475(2) . ?
Nd1 O5 2.500(2) . ?
Nd1 O7 2.5121(19) . ?
Nd1 O4 2.531(2) . ?
Nd1 N1 2.657(2) . ?
Nd1 N3 2.683(2) . ?
O2 C12 1.247(3) . ?
O1 C6 1.240(3) . ?
N3 C11 1.336(4) . ?
N3 C7 1.345(3) . ?
N2 C6 1.321(4) . ?
N1 C5 1.337(3) . ?
N1 C1 1.347(3) . ?
C5 C4 1.385(4) . ?
C12 N4 1.312(4) . ?
C12 C7 1.499(4) . ?
C7 C8 1.386(4) . ?
C1 C2 1.385(4) . ?
C1 C6 1.506(4) . ?
C2 C3 1.392(4) . ?
C10 C9 1.385(4) . ?
C10 C11 1.388(4) . ?
C4 C3 1.373(4) . ?
C8 C9 1.385(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Nd1 O2 115.92(7) . . ?
O1 Nd1 O6 70.98(7) . . ?
O2 Nd1 O6 69.57(7) . . ?
O1 Nd1 O3 74.69(7) . . ?
O2 Nd1 O3 130.12(7) . . ?
O6 Nd1 O3 145.60(7) . . ?
O1 Nd1 O5 134.06(7) . . ?
O2 Nd1 O5 74.60(7) . . ?
O6 Nd1 O5 72.34(7) . . ?
O3 Nd1 O5 134.98(7) . . ?
O1 Nd1 O7 67.23(6) . . ?
O2 Nd1 O7 68.56(7) . . ?
O6 Nd1 O7 95.33(7) . . ?
O3 Nd1 O7 73.05(7) . . ?
O5 Nd1 O7 143.15(7) . . ?
O1 Nd1 O4 121.75(7) . . ?
O2 Nd1 O4 122.32(7) . . ?
O6 Nd1 O4 130.39(7) . . ?
O3 Nd1 O4 68.11(7) . . ?
O5 Nd1 O4 66.97(7) . . ?
O7 Nd1 O4 134.28(7) . . ?
O1 Nd1 N1 62.33(6) . . ?
O2 Nd1 N1 143.99(6) . . ?
O6 Nd1 N1 76.90(7) . . ?
O3 Nd1 N1 85.45(8) . . ?
O5 Nd1 N1 83.21(8) . . ?
O7 Nd1 N1 128.75(7) . . ?
O4 Nd1 N1 71.37(7) . . ?
O1 Nd1 N3 143.85(7) . . ?
O2 Nd1 N3 61.81(7) . . ?
O6 Nd1 N3 129.35(7) . . ?
O3 Nd1 N3 81.48(8) . . ?
O5 Nd1 N3 81.76(8) . . ?
O7 Nd1 N3 80.12(7) . . ?
O4 Nd1 N3 71.28(7) . . ?
N1 Nd1 N3 142.64(7) . . ?
C12 O2 Nd1 126.90(18) . . ?
C6 O1 Nd1 127.92(17) . . ?
C11 N3 C7 117.3(2) . . ?
C11 N3 Nd1 125.47(19) . . ?
C7 N3 Nd1 116.68(17) . . ?
C5 N1 C1 117.4(2) . . ?
C5 N1 Nd1 124.89(18) . . ?
C1 N1 Nd1 117.54(16) . . ?
N1 C5 C4 123.1(3) . . ?
O2 C12 N4 121.8(3) . . ?
O2 C12 C7 118.7(2) . . ?
N4 C12 C7 119.4(2) . . ?
N3 C7 C8 122.8(3) . . ?
N3 C7 C12 113.3(2) . . ?
C8 C7 C12 123.9(2) . . ?
N1 C1 C2 123.0(2) . . ?
N1 C1 C6 112.9(2) . . ?
C2 C1 C6 124.2(2) . . ?
C1 C2 C3 118.5(3) . . ?
C9 C10 C11 118.4(3) . . ?
O1 C6 N2 121.6(3) . . ?
O1 C6 C1 118.6(2) . . ?
N2 C6 C1 119.8(2) . . ?
C3 C4 C5 119.0(3) . . ?
C9 C8 C7 119.0(3) . . ?
N3 C11 C10 123.6(3) . . ?
C8 C9 C10 118.8(3) . . ?
C4 C3 C2 118.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.865
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.091


_database_code_depnum_ccdc_archive 'CCDC 918185'
#######################################################################
#
#                 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_mx1439-b
#TrackingRef 'mx1439-b.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 Pr O7,3(Cl)'
_chemical_formula_sum            'C12 H22 Cl3 N4 O7 Pr'
_chemical_formula_weight         581.60

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'
Cl Cl 0.1484 0.1585 '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   C2/c

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

_cell_length_a                   28.794(6)
_cell_length_b                   7.7507(16)
_cell_length_c                   19.683(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.34(3)
_cell_angle_gamma                90.00
_cell_volume                     4255.8(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7497
_cell_measurement_theta_min      1.0678
_cell_measurement_theta_max      27.4711

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2304
_exptl_absorpt_coefficient_mu    2.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4924
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14466
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4841
_reflns_number_gt                4344
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0259P)²+13.8105P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4841
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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 0.108063(8) 0.77281(3) 0.206112(11) 0.02161(8) Uani 1 1 d . . .
Cl1 Cl 0.06274(4) 0.28796(14) 0.06780(5) 0.0289(2) Uani 1 1 d . . .
Cl2 Cl 0.06241(4) 0.24783(14) 0.31185(5) 0.0292(2) Uani 1 1 d . . .
Cl3 Cl 0.25058(4) 0.03902(15) 0.35160(5) 0.0324(3) Uani 1 1 d . . .
O1 O 0.06266(11) 0.7482(4) 0.08441(14) 0.0263(7) Uani 1 1 d . . .
O5 O 0.19918(11) 0.7700(4) 0.24045(16) 0.0323(7) Uani 1 1 d . . .
H5A H 0.2200 0.7868 0.2781 0.039 Uiso 1 1 d R . .
H5B H 0.2172 0.7143 0.2207 0.039 Uiso 1 1 d R . .
O3 O 0.04520(10) 1.0080(4) 0.17374(14) 0.0265(7) Uani 1 1 d . . .
H3A H 0.0378 1.0527 0.2085 0.032 Uiso 1 1 d R . .
H3B H 0.0531 1.0854 0.1489 0.032 Uiso 1 1 d R . .
O4 O 0.04961(11) 0.5324(4) 0.19330(15) 0.0300(7) Uani 1 1 d . . .
H4A H 0.0460 0.4625 0.2242 0.036 Uiso 1 1 d R . .
H4B H 0.0538 0.4664 0.1615 0.036 Uiso 1 1 d R . .
O2 O 0.06151(11) 0.8063(4) 0.29239(15) 0.0301(7) Uani 1 1 d . . .
O7 O 0.14305(11) 0.5170(4) 0.15748(18) 0.0393(8) Uani 1 1 d . . .
H7A H 0.1245 0.4405 0.1358 0.047 Uiso 1 1 d R . .
H7B H 0.1708 0.5024 0.1520 0.047 Uiso 1 1 d R . .
O6 O 0.14151(11) 1.0348(4) 0.27532(18) 0.0395(9) Uani 1 1 d . . .
H6A H 0.1182 1.0804 0.2871 0.047 Uiso 1 1 d R . .
H6B H 0.1713 1.0469 0.2896 0.047 Uiso 1 1 d R . .
N1 N 0.14068(13) 0.9385(5) 0.10634(18) 0.0274(8) Uani 1 1 d . . .
N3 N 0.13684(13) 0.6035(5) 0.32748(17) 0.0255(8) Uani 1 1 d . . .
N4 N 0.04454(14) 0.7900(5) 0.39698(18) 0.0310(9) Uani 1 1 d . . .
H4C H 0.0192 0.8563 0.3827 0.037 Uiso 1 1 calc R . .
H4D H 0.0520 0.7497 0.4401 0.037 Uiso 1 1 calc R . .
N2 N 0.05191(15) 0.7433(5) -0.03215(19) 0.0366(10) Uani 1 1 d . . .
H2C H 0.0253 0.6829 -0.0378 0.044 Uiso 1 1 calc R . .
H2D H 0.0623 0.7736 -0.0689 0.044 Uiso 1 1 calc R . .
C12 C 0.07123(17) 0.7511(5) 0.3538(2) 0.0260(9) Uani 1 1 d . . .
C6 C 0.07598(16) 0.7881(5) 0.0310(2) 0.0251(9) Uani 1 1 d . . .
C7 C 0.11429(15) 0.6372(5) 0.3779(2) 0.0238(9) Uani 1 1 d . . .
C1 C 0.12089(15) 0.8937(6) 0.0389(2) 0.0256(9) Uani 1 1 d . . .
C11 C 0.17441(16) 0.4942(6) 0.3429(2) 0.0305(10) Uani 1 1 d . . .
H11 H 0.1900 0.4655 0.3071 0.037 Uiso 1 1 calc R . .
C5 C 0.17845(17) 1.0440(6) 0.1182(2) 0.0330(11) Uani 1 1 d . . .
H5 H 0.1923 1.0783 0.1652 0.040 Uiso 1 1 calc R . .
C2 C 0.13935(16) 0.9455(6) -0.0163(2) 0.0291(10) Uani 1 1 d . . .
H2 H 0.1248 0.9094 -0.0629 0.035 Uiso 1 1 calc R . .
C10 C 0.19115(17) 0.4221(6) 0.4092(2) 0.0328(11) Uani 1 1 d . . .
H10 H 0.2174 0.3442 0.4180 0.039 Uiso 1 1 calc R . .
C8 C 0.12940(16) 0.5724(6) 0.4457(2) 0.0286(10) Uani 1 1 d . . .
H8 H 0.1129 0.6010 0.4804 0.034 Uiso 1 1 calc R . .
C3 C 0.17949(18) 1.0513(6) -0.0025(3) 0.0355(11) Uani 1 1 d . . .
H3 H 0.1937 1.0854 -0.0391 0.043 Uiso 1 1 calc R . .
C9 C 0.16956(17) 0.4639(6) 0.4615(2) 0.0337(11) Uani 1 1 d . . .
H9 H 0.1816 0.4203 0.5076 0.040 Uiso 1 1 calc R . .
C4 C 0.19862(17) 1.1065(6) 0.0660(2) 0.0350(11) Uani 1 1 d . . .
H4 H 0.2248 1.1848 0.0768 0.042 Uiso 1 1 calc 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 O2 2.424(3) . ?
Pr1 O1 2.436(3) . ?
Pr1 O4 2.481(3) . ?
Pr1 O6 2.501(3) . ?
Pr1 O7 2.518(3) . ?
Pr1 O3 2.537(3) . ?
Pr1 O5 2.542(3) . ?
Pr1 N3 2.671(3) . ?
Pr1 N1 2.702(4) . ?
O1 C6 1.245(5) . ?
O2 C12 1.248(5) . ?
N1 C5 1.334(6) . ?
N1 C1 1.354(5) . ?
N3 C7 1.339(5) . ?
N3 C11 1.348(6) . ?
N4 C12 1.314(6) . ?
N2 C6 1.311(5) . ?
C12 C7 1.500(6) . ?
C6 C1 1.505(6) . ?
C7 C8 1.391(5) . ?
C1 C2 1.382(6) . ?
C11 C10 1.391(6) . ?
C5 C4 1.386(7) . ?
C2 C3 1.388(7) . ?
C10 C9 1.368(7) . ?
C8 C9 1.401(6) . ?
C3 C4 1.392(6) . ?

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 O1 116.24(10) . . ?
O2 Pr1 O4 70.89(10) . . ?
O1 Pr1 O4 69.88(10) . . ?
O2 Pr1 O6 74.74(11) . . ?
O1 Pr1 O6 129.76(10) . . ?
O4 Pr1 O6 145.57(11) . . ?
O2 Pr1 O7 133.89(11) . . ?
O1 Pr1 O7 74.48(10) . . ?
O4 Pr1 O7 72.26(11) . . ?
O6 Pr1 O7 135.23(10) . . ?
O2 Pr1 O3 67.36(10) . . ?
O1 Pr1 O3 68.49(9) . . ?
O4 Pr1 O3 95.18(10) . . ?
O6 Pr1 O3 73.01(10) . . ?
O7 Pr1 O3 142.96(10) . . ?
O2 Pr1 O5 121.87(10) . . ?
O1 Pr1 O5 121.87(11) . . ?
O4 Pr1 O5 130.55(10) . . ?
O6 Pr1 O5 68.24(10) . . ?
O7 Pr1 O5 67.09(10) . . ?
O3 Pr1 O5 134.27(10) . . ?
O2 Pr1 N3 61.90(11) . . ?
O1 Pr1 N3 144.41(10) . . ?
O4 Pr1 N3 76.96(10) . . ?
O6 Pr1 N3 85.39(11) . . ?
O7 Pr1 N3 83.59(11) . . ?
O3 Pr1 N3 128.45(10) . . ?
O5 Pr1 N3 71.76(11) . . ?
O2 Pr1 N1 144.14(11) . . ?
O1 Pr1 N1 61.37(10) . . ?
O4 Pr1 N1 129.20(10) . . ?
O6 Pr1 N1 81.59(12) . . ?
O7 Pr1 N1 81.61(12) . . ?
O3 Pr1 N1 80.26(10) . . ?
O5 Pr1 N1 71.07(11) . . ?
N3 Pr1 N1 142.82(11) . . ?
C6 O1 Pr1 127.5(3) . . ?
C12 O2 Pr1 127.8(3) . . ?
C5 N1 C1 117.1(4) . . ?
C5 N1 Pr1 125.4(3) . . ?
C1 N1 Pr1 117.0(3) . . ?
C7 N3 C11 117.8(4) . . ?
C7 N3 Pr1 117.8(3) . . ?
C11 N3 Pr1 124.3(3) . . ?
O2 C12 N4 121.4(4) . . ?
O2 C12 C7 118.5(4) . . ?
N4 C12 C7 120.1(4) . . ?
O1 C6 N2 122.3(4) . . ?
O1 C6 C1 119.0(4) . . ?
N2 C6 C1 118.8(4) . . ?
N3 C7 C8 123.1(4) . . ?
N3 C7 C12 113.3(4) . . ?
C8 C7 C12 123.5(4) . . ?
N1 C1 C2 123.1(4) . . ?
N1 C1 C6 112.5(4) . . ?
C2 C1 C6 124.4(4) . . ?
N3 C11 C10 122.4(5) . . ?
N1 C5 C4 123.9(4) . . ?
C1 C2 C3 118.8(4) . . ?
C9 C10 C11 119.7(4) . . ?
C7 C8 C9 118.3(4) . . ?
C2 C3 C4 118.8(5) . . ?
C10 C9 C8 118.7(4) . . ?
C5 C4 C3 118.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.132


_database_code_depnum_ccdc_archive 'CCDC 918186'
#######################################################################
#
#                 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_1633
#TrackingRef '1633.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 Sm O7,3(Cl)'
_chemical_formula_sum            'C12 H22 Cl3 N4 O7 Sm'
_chemical_formula_weight         591.04

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.712(6)
_cell_length_b                   7.7286(15)
_cell_length_c                   19.559(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.11(3)
_cell_angle_gamma                90.00
_cell_volume                     4209.1(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6267
_cell_measurement_theta_min      1.4626
_cell_measurement_theta_max      27.4747

_exptl_crystal_description       plate
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.052
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2328
_exptl_absorpt_coefficient_mu    3.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4672
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10409
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4779
_reflns_number_gt                4373
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0704P)²+167.8820P] 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         4779
_refine_ls_number_parameters     286
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0747
_refine_ls_wR_factor_ref         0.2011
_refine_ls_wR_factor_gt          0.1904
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.178
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm1 Sm 0.608132(18) 0.27263(7) 0.20565(3) 0.02082(18) Uani 1 1 d . . .
Cl1 Cl 0.56301(9) 0.7883(3) 0.06722(13) 0.0278(5) Uani 1 1 d . . .
Cl2 Cl 0.56278(10) 0.7482(3) 0.31174(13) 0.0279(5) Uani 1 1 d . . .
Cl3 Cl 0.74961(9) 0.0358(4) 0.14830(14) 0.0309(6) Uani 1 1 d . . .
O1 O 0.5627(3) 0.2450(10) 0.0859(4) 0.0280(16) Uani 1 1 d . . .
O5 O 0.6986(2) 0.2701(11) 0.2393(4) 0.0293(17) Uani 1 1 d D . .
H15A H 0.714(4) 0.252(16) 0.208(5) 0.035 Uiso 1 1 d D . .
H15B H 0.709(4) 0.306(17) 0.281(3) 0.035 Uiso 1 1 d D . .
O3 O 0.5466(3) 0.5056(9) 0.1741(4) 0.0239(15) Uani 1 1 d D . .
H13B H 0.550(4) 0.572(13) 0.141(4) 0.029 Uiso 1 1 d D . .
H13A H 0.540(4) 0.549(15) 0.210(4) 0.029 Uiso 1 1 d D . .
O2 O 0.5621(3) 0.3078(11) 0.2902(4) 0.0301(17) Uani 1 1 d . . .
O6 O 0.5504(3) 0.0367(10) 0.1941(4) 0.0283(16) Uani 1 1 d D . .
H16A H 0.552(5) -0.040(12) 0.225(5) 0.034 Uiso 1 1 d D . .
H16B H 0.547(5) -0.012(15) 0.155(3) 0.034 Uiso 1 1 d D . .
N3 N 0.6404(3) 0.4367(12) 0.1072(5) 0.0258(18) Uani 1 1 d . . .
O7 O 0.6420(3) 0.0212(12) 0.1568(5) 0.0370(19) Uani 1 1 d D . .
H17B H 0.651(5) -0.003(19) 0.120(4) 0.044 Uiso 1 1 d D . .
H17A H 0.6716(12) 0.031(19) 0.174(7) 0.044 Uiso 1 1 d D . .
N1 N 0.6368(3) 0.1036(12) 0.3245(5) 0.0273(19) Uani 1 1 d . . .
O4 O 0.6408(3) 0.5279(11) 0.2740(5) 0.0365(19) Uani 1 1 d D . .
H14B H 0.624(4) 0.588(15) 0.296(7) 0.044 Uiso 1 1 d D . .
H14A H 0.667(3) 0.559(18) 0.302(6) 0.044 Uiso 1 1 d D . .
N4 N 0.5522(4) 0.2408(15) -0.0321(5) 0.035(2) Uani 1 1 d D . .
H24B H 0.563(5) 0.251(17) -0.071(5) 0.042 Uiso 1 1 d D . .
H24A H 0.526(3) 0.183(16) -0.028(7) 0.042 Uiso 1 1 d D . .
N2 N 0.5448(3) 0.2905(13) 0.3960(5) 0.029(2) Uani 1 1 d D . .
H22A H 0.535(3) 0.401(6) 0.387(4) 0.035 Uiso 1 1 d D . .
H22B H 0.549(3) 0.244(10) 0.440(3) 0.035 Uiso 1 1 d D . .
C12 C 0.5761(4) 0.2847(14) 0.0324(5) 0.023(2) Uani 1 1 d . . .
C6 C 0.5714(4) 0.2538(14) 0.3516(5) 0.027(2) Uani 1 1 d D . .
C1 C 0.6143(3) 0.1382(13) 0.3759(5) 0.023(2) Uani 1 1 d . . .
C7 C 0.6209(4) 0.3924(13) 0.0403(5) 0.025(2) Uani 1 1 d . . .
C2 C 0.6301(4) 0.0734(14) 0.4438(5) 0.026(2) Uani 1 1 d . . .
H2 H 0.6136 0.1015 0.4790 0.031 Uiso 1 1 calc R . .
C8 C 0.6401(4) 0.4456(15) -0.0150(5) 0.028(2) Uani 1 1 d . . .
H8 H 0.6258 0.4086 -0.0617 0.033 Uiso 1 1 calc R . .
C5 C 0.6742(4) -0.0063(14) 0.3399(6) 0.028(2) Uani 1 1 d . . .
H5 H 0.6894 -0.0367 0.3036 0.034 Uiso 1 1 calc R . .
C9 C 0.6794(4) 0.5503(15) -0.0025(7) 0.035(3) Uani 1 1 d . . .
H9 H 0.6934 0.5839 -0.0397 0.042 Uiso 1 1 calc R . .
C4 C 0.6916(4) -0.0779(14) 0.4067(5) 0.026(2) Uani 1 1 d . . .
H4 H 0.7179 -0.1563 0.4154 0.031 Uiso 1 1 calc R . .
C11 C 0.6780(4) 0.5443(15) 0.1189(6) 0.031(2) Uani 1 1 d . . .
H11 H 0.6916 0.5801 0.1661 0.037 Uiso 1 1 calc R . .
C10 C 0.6985(4) 0.6069(15) 0.0661(6) 0.031(2) Uani 1 1 d . . .
H10 H 0.7246 0.6858 0.0766 0.038 Uiso 1 1 calc R . .
C3 C 0.6702(4) -0.0328(15) 0.4597(6) 0.033(2) Uani 1 1 d . . .
H3 H 0.6826 -0.0737 0.5064 0.040 Uiso 1 1 calc 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
Sm1 O2 2.370(7) . ?
Sm1 O1 2.396(7) . ?
Sm1 O6 2.437(8) . ?
Sm1 O4 2.439(8) . ?
Sm1 O7 2.468(8) . ?
Sm1 O3 2.492(7) . ?
Sm1 O5 2.520(7) . ?
Sm1 N1 2.618(9) . ?
Sm1 N3 2.654(9) . ?
O1 C12 1.239(12) . ?
O2 C6 1.237(12) . ?
N3 C7 1.335(13) . ?
N3 C11 1.339(14) . ?
N1 C5 1.344(14) . ?
N1 C1 1.347(13) . ?
N4 C12 1.324(14) . ?
N2 C6 1.319(14) . ?
C12 C7 1.507(15) . ?
C6 C1 1.503(15) . ?
C1 C2 1.388(14) . ?
C7 C8 1.392(14) . ?
C2 C3 1.386(15) . ?
C8 C9 1.361(16) . ?
C5 C4 1.395(14) . ?
C9 C10 1.389(17) . ?
C4 C3 1.373(16) . ?
C11 C10 1.394(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Sm1 O1 115.4(3) . . ?
O2 Sm1 O6 70.6(3) . . ?
O1 Sm1 O6 69.3(3) . . ?
O2 Sm1 O4 74.3(3) . . ?
O1 Sm1 O4 130.8(3) . . ?
O6 Sm1 O4 144.8(3) . . ?
O2 Sm1 O7 134.4(3) . . ?
O1 Sm1 O7 73.9(3) . . ?
O6 Sm1 O7 72.4(3) . . ?
O4 Sm1 O7 135.6(3) . . ?
O2 Sm1 O3 66.9(2) . . ?
O1 Sm1 O3 68.8(2) . . ?
O6 Sm1 O3 95.3(3) . . ?
O4 Sm1 O3 72.9(3) . . ?
O7 Sm1 O3 142.7(3) . . ?
O2 Sm1 O5 122.2(3) . . ?
O1 Sm1 O5 122.4(3) . . ?
O6 Sm1 O5 130.8(3) . . ?
O4 Sm1 O5 68.2(3) . . ?
O7 Sm1 O5 67.5(3) . . ?
O3 Sm1 O5 133.9(3) . . ?
O2 Sm1 N1 63.0(3) . . ?
O1 Sm1 N1 143.3(3) . . ?
O6 Sm1 N1 76.6(3) . . ?
O4 Sm1 N1 85.5(3) . . ?
O7 Sm1 N1 83.3(3) . . ?
O3 Sm1 N1 129.1(2) . . ?
O5 Sm1 N1 71.5(3) . . ?
O2 Sm1 N3 143.5(3) . . ?
O1 Sm1 N3 62.4(3) . . ?
O6 Sm1 N3 129.8(3) . . ?
O4 Sm1 N3 81.7(3) . . ?
O7 Sm1 N3 81.7(3) . . ?
O3 Sm1 N3 80.0(2) . . ?
O5 Sm1 N3 70.9(3) . . ?
N1 Sm1 N3 142.5(3) . . ?
C12 O1 Sm1 126.7(7) . . ?
C6 O2 Sm1 127.8(7) . . ?
C7 N3 C11 117.1(9) . . ?
C7 N3 Sm1 116.8(7) . . ?
C11 N3 Sm1 125.6(7) . . ?
C5 N1 C1 117.4(9) . . ?
C5 N1 Sm1 125.1(7) . . ?
C1 N1 Sm1 117.4(7) . . ?
O1 C12 N4 123.0(10) . . ?
O1 C12 C7 118.8(9) . . ?
N4 C12 C7 118.1(9) . . ?
O2 C6 N2 123.0(11) . . ?
O2 C6 C1 118.3(10) . . ?
N2 C6 C1 118.7(9) . . ?
N1 C1 C2 122.6(10) . . ?
N1 C1 C6 112.7(9) . . ?
C2 C1 C6 124.6(9) . . ?
N3 C7 C8 122.3(10) . . ?
N3 C7 C12 112.7(9) . . ?
C8 C7 C12 124.9(10) . . ?
C3 C2 C1 119.1(10) . . ?
C9 C8 C7 120.2(10) . . ?
N1 C5 C4 123.0(10) . . ?
C8 C9 C10 118.4(10) . . ?
C3 C4 C5 118.8(10) . . ?
N3 C11 C10 123.8(10) . . ?
C9 C10 C11 117.9(11) . . ?
C4 C3 C2 118.8(10) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         3.550
_refine_diff_density_min         -1.829
_refine_diff_density_rms         0.305


_database_code_depnum_ccdc_archive 'CCDC 918187'
#######################################################################
#
#                 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_sa1844
#TrackingRef 'sa1844.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 Gd N4 O7, 3(Cl)'
_chemical_formula_sum            'C12 H22 Cl3 Gd N4 O7'
_chemical_formula_weight         597.94

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Gd Gd -0.1653 3.9035 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   28.616(6)
_cell_length_b                   7.7264(15)
_cell_length_c                   19.526(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.04(3)
_cell_angle_gamma                90.00
_cell_volume                     4188.1(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7122
_cell_measurement_theta_min      1.5947
_cell_measurement_theta_max      27.4812

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.897
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2344
_exptl_absorpt_coefficient_mu    3.589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7425
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15503
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4784
_reflns_number_gt                4570
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0547P)²+9.3904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4784
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_restrained_S_all      1.238
_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
Gd1 Gd 0.108099(8) 0.72714(3) 0.205519(11) 0.01821(10) Uani 1 1 d . . .
O1 O 0.06257(13) 0.7585(4) 0.08620(19) 0.0231(8) Uani 1 1 d . . .
O2 O 0.06209(12) 0.6902(5) 0.28988(18) 0.0236(7) Uani 1 1 d . . .
N4 N 0.04451(16) 0.7072(6) 0.3953(2) 0.0262(9) Uani 1 1 d . . .
H4C H 0.0196 0.6421 0.3815 0.031 Uiso 1 1 calc R . .
H4D H 0.0518 0.7471 0.4376 0.031 Uiso 1 1 calc R . .
N1 N 0.14023(14) 0.5625(5) 0.1082(2) 0.0229(8) Uani 1 1 d . . .
C11 C 0.17418(17) 1.0048(6) 0.3392(3) 0.0256(10) Uani 1 1 d . . .
H11 H 0.1893 1.0334 0.3036 0.031 Uiso 1 1 calc R . .
C6 C 0.07659(18) 0.7175(6) 0.0325(3) 0.0218(10) Uani 1 1 d . . .
N2 N 0.05211(18) 0.7621(6) -0.0315(2) 0.0307(11) Uani 1 1 d . . .
H2A H 0.0259 0.8206 -0.0370 0.037 Uiso 1 1 calc R . .
H2B H 0.0624 0.7325 -0.0677 0.037 Uiso 1 1 calc R . .
C1 C 0.12069(17) 0.6083(6) 0.0404(2) 0.0216(9) Uani 1 1 d . . .
N3 N 0.13713(14) 0.8957(5) 0.3238(2) 0.0224(8) Uani 1 1 d . . .
C2 C 0.13963(18) 0.5564(7) -0.0152(3) 0.0271(10) Uani 1 1 d . . .
H2 H 0.1258 0.5932 -0.0610 0.032 Uiso 1 1 calc R . .
C7 C 0.11461(16) 0.8595(6) 0.3756(2) 0.0204(9) Uani 1 1 d . . .
C12 C 0.07140(18) 0.7454(6) 0.3516(3) 0.0203(10) Uani 1 1 d . . .
C10 C 0.19153(18) 1.0784(6) 0.4055(3) 0.0268(10) Uani 1 1 d . . .
H10 H 0.2170 1.1567 0.4135 0.032 Uiso 1 1 calc R . .
C5 C 0.17779(17) 0.4545(7) 0.1194(3) 0.0278(11) Uani 1 1 d . . .
H5 H 0.1911 0.4182 0.1654 0.033 Uiso 1 1 calc R . .
C4 C 0.19795(19) 0.3938(7) 0.0667(3) 0.0319(12) Uani 1 1 d . . .
H4 H 0.2237 0.3168 0.0770 0.038 Uiso 1 1 calc R . .
C8 C 0.13041(18) 0.9254(6) 0.4437(2) 0.0244(10) Uani 1 1 d . . .
H8 H 0.1144 0.8978 0.4785 0.029 Uiso 1 1 calc R . .
C3 C 0.17951(19) 0.4487(7) -0.0012(3) 0.0294(11) Uani 1 1 d . . .
H3 H 0.1935 0.4143 -0.0373 0.035 Uiso 1 1 calc R . .
C9 C 0.17036(18) 1.0330(7) 0.4587(3) 0.0266(10) Uani 1 1 d . . .
H9 H 0.1826 1.0738 0.5044 0.032 Uiso 1 1 calc R . .
Cl2 Cl 0.06291(5) 0.25245(15) 0.31139(7) 0.0254(3) Uani 1 1 d . . .
Cl3 Cl 0.25045(4) 0.46501(17) 0.35145(6) 0.0278(3) Uani 1 1 d . . .
O3 O 0.19769(14) 0.7301(4) 0.2385(2) 0.0278(8) Uani 1 1 d . . .
H3B H 0.2149 0.7751 0.2140 0.033 Uiso 1 1 d R . .
H3A H 0.2163 0.6819 0.2731 0.033 Uiso 1 1 d R . .
O5 O 0.04730(12) 0.4973(4) 0.17355(16) 0.0227(7) Uani 1 1 d . . .
H5B H 0.0525 0.4238 0.1446 0.027 Uiso 1 1 d R . .
H5A H 0.0404 0.4491 0.2084 0.027 Uiso 1 1 d R . .
O7 O 0.05109(12) 0.9614(5) 0.19443(18) 0.0258(7) Uani 1 1 d . . .
H7A H 0.0438 1.0355 0.1621 0.031 Uiso 1 1 d R . .
H7B H 0.0424 0.9903 0.2309 0.031 Uiso 1 1 d R . .
O6 O 0.14230(12) 0.9769(5) 0.1578(2) 0.0325(9) Uani 1 1 d . . .
H6A H 0.1683 0.9841 0.1451 0.039 Uiso 1 1 d R . .
H6B H 0.1258 1.0492 0.1300 0.039 Uiso 1 1 d R . .
O4 O 0.14070(12) 0.4735(5) 0.2733(2) 0.0315(8) Uani 1 1 d . . .
H4B H 0.1673 0.4698 0.3033 0.038 Uiso 1 1 d R . .
H4A H 0.1276 0.4146 0.2997 0.038 Uiso 1 1 d R . .
Cl1 Cl 0.06314(5) 0.21018(15) 0.06756(6) 0.0245(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O2 2.362(3) . ?
Gd1 O1 2.390(4) . ?
Gd1 O7 2.411(3) . ?
Gd1 O4 2.421(3) . ?
Gd1 O6 2.448(4) . ?
Gd1 O5 2.458(3) . ?
Gd1 O3 2.487(4) . ?
Gd1 N3 2.606(4) . ?
Gd1 N1 2.631(4) . ?
O1 C6 1.251(6) . ?
O2 C12 1.246(6) . ?
N4 C12 1.313(7) . ?
N1 C5 1.336(6) . ?
N1 C1 1.353(6) . ?
C11 N3 1.330(6) . ?
C11 C10 1.391(7) . ?
C6 N2 1.322(7) . ?
C6 C1 1.494(7) . ?
C1 C2 1.386(7) . ?
N3 C7 1.353(6) . ?
C2 C3 1.385(7) . ?
C7 C8 1.394(6) . ?
C7 C12 1.498(7) . ?
C10 C9 1.370(7) . ?
C5 C4 1.379(7) . ?
C4 C3 1.369(8) . ?
C8 C9 1.386(7) . ?

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 Gd1 O1 115.33(12) . . ?
O2 Gd1 O7 70.97(12) . . ?
O1 Gd1 O7 68.86(11) . . ?
O2 Gd1 O4 74.15(12) . . ?
O1 Gd1 O4 131.44(12) . . ?
O7 Gd1 O4 145.00(12) . . ?
O2 Gd1 O6 134.64(13) . . ?
O1 Gd1 O6 73.90(12) . . ?
O7 Gd1 O6 72.44(12) . . ?
O4 Gd1 O6 135.19(11) . . ?
O2 Gd1 O5 67.04(11) . . ?
O1 Gd1 O5 68.95(11) . . ?
O7 Gd1 O5 95.61(12) . . ?
O4 Gd1 O5 73.11(11) . . ?
O6 Gd1 O5 142.80(11) . . ?
O2 Gd1 O3 122.32(13) . . ?
O1 Gd1 O3 122.36(13) . . ?
O7 Gd1 O3 130.44(12) . . ?
O4 Gd1 O3 68.28(11) . . ?
O6 Gd1 O3 66.98(11) . . ?
O5 Gd1 O3 133.95(11) . . ?
O2 Gd1 N3 63.52(12) . . ?
O1 Gd1 N3 142.61(12) . . ?
O7 Gd1 N3 76.56(12) . . ?
O4 Gd1 N3 85.53(13) . . ?
O6 Gd1 N3 82.67(13) . . ?
O5 Gd1 N3 129.79(12) . . ?
O3 Gd1 N3 71.28(13) . . ?
O2 Gd1 N1 142.82(12) . . ?
O1 Gd1 N1 63.15(12) . . ?
O7 Gd1 N1 130.20(12) . . ?
O4 Gd1 N1 81.26(13) . . ?
O6 Gd1 N1 82.19(13) . . ?
O5 Gd1 N1 79.47(12) . . ?
O3 Gd1 N1 70.88(13) . . ?
N3 Gd1 N1 142.16(12) . . ?
C6 O1 Gd1 125.6(3) . . ?
C12 O2 Gd1 127.5(3) . . ?
C5 N1 C1 116.6(4) . . ?
C5 N1 Gd1 126.3(3) . . ?
C1 N1 Gd1 116.5(3) . . ?
N3 C11 C10 123.6(5) . . ?
O1 C6 N2 121.5(5) . . ?
O1 C6 C1 119.4(4) . . ?
N2 C6 C1 119.1(5) . . ?
N1 C1 C2 122.9(5) . . ?
N1 C1 C6 112.8(4) . . ?
C2 C1 C6 124.3(4) . . ?
C11 N3 C7 117.4(4) . . ?
C11 N3 Gd1 125.6(3) . . ?
C7 N3 Gd1 116.8(3) . . ?
C3 C2 C1 118.7(5) . . ?
N3 C7 C8 122.3(4) . . ?
N3 C7 C12 113.3(4) . . ?
C8 C7 C12 124.4(4) . . ?
O2 C12 N4 122.0(5) . . ?
O2 C12 C7 118.1(5) . . ?
N4 C12 C7 120.0(5) . . ?
C9 C10 C11 118.6(5) . . ?
N1 C5 C4 123.8(5) . . ?
C3 C4 C5 119.0(5) . . ?
C9 C8 C7 118.8(5) . . ?
C4 C3 C2 118.8(5) . . ?
C10 C9 C8 119.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.163
_refine_diff_density_min         -1.372
_refine_diff_density_rms         0.250


_database_code_depnum_ccdc_archive 'CCDC 918190'
#######################################################################
#
#                 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_1264-2
#TrackingRef '1264-2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 Er N4 O6,3(Cl),H2 O'
_chemical_formula_sum            'C12 H22 Cl3 Er N4 O7'
_chemical_formula_weight         607.95

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 '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                   8.6514(17)
_cell_length_b                   9.1529(18)
_cell_length_c                   14.048(3)
_cell_angle_alpha                96.25(3)
_cell_angle_beta                 99.78(3)
_cell_angle_gamma                105.83(3)
_cell_volume                     1040.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4237
_cell_measurement_theta_min      1.4910
_cell_measurement_theta_max      27.4843

_exptl_crystal_description       rod
_exptl_crystal_colour            'light pink'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             594
_exptl_absorpt_coefficient_mu    4.458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7103
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  'MM007HF + CCD (Saturn724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13460
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0344
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4760
_reflns_number_gt                4663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0314P)²+0.6341P] 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         4760
_refine_ls_number_parameters     300
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0684
_refine_ls_wR_factor_gt          0.0679
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.200
_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
Er1 Er 0.752291(15) 0.597024(15) 0.779809(9) 0.01468(6) Uani 1 1 d . . .
Cl1 Cl 0.79598(10) 0.14448(10) 0.56068(6) 0.02229(17) Uani 1 1 d . . .
Cl2 Cl 0.27655(10) 0.52955(10) 0.87941(6) 0.02439(18) Uani 1 1 d . . .
Cl3 Cl 0.54417(11) 0.04819(10) 0.79788(7) 0.02632(18) Uani 1 1 d . . .
O6 O 0.6009(3) 0.4543(3) 0.88300(18) 0.0197(5) Uani 1 1 d D . .
O1 O 0.9258(3) 0.6082(3) 0.92282(17) 0.0185(5) Uani 1 1 d . . .
O3 O 0.5916(3) 0.7414(3) 0.83562(19) 0.0219(5) Uani 1 1 d D . .
O4 O 0.9888(3) 0.5975(3) 0.71615(19) 0.0224(5) Uani 1 1 d D . .
O5 O 0.7574(3) 0.3435(3) 0.74188(19) 0.0221(5) Uani 1 1 d D . .
O2 O 0.7114(3) 0.7248(3) 0.65319(16) 0.0196(5) Uani 1 1 d . . .
N1 N 0.9544(3) 0.8592(3) 0.8431(2) 0.0173(5) Uani 1 1 d . . .
N3 N 0.4820(3) 0.4742(3) 0.6645(2) 0.0189(6) Uani 1 1 d . . .
N2 N 1.1314(4) 0.7203(4) 1.0504(2) 0.0218(6) Uani 1 1 d D . .
O7 O 0.1851(4) 0.8480(4) 0.6660(2) 0.0371(7) Uani 1 1 d . . .
N4 N 0.5399(4) 0.8124(3) 0.5527(2) 0.0213(6) Uani 1 1 d D . .
C5 C 0.9681(4) 0.9838(4) 0.7997(2) 0.0210(7) Uani 1 1 d . . .
H5 H 0.8865 0.9802 0.7442 0.025 Uiso 1 1 calc R . .
C1 C 1.0731(4) 0.8666(4) 0.9221(2) 0.0172(6) Uani 1 1 d . . .
C7 C 0.4355(4) 0.5632(4) 0.6018(2) 0.0178(6) Uani 1 1 d . . .
C12 C 0.5708(4) 0.7087(4) 0.6032(2) 0.0180(6) Uani 1 1 d . . .
C8 C 0.2823(4) 0.5223(4) 0.5409(3) 0.0226(7) Uani 1 1 d . . .
H8 H 0.2532 0.5885 0.4981 0.027 Uiso 1 1 calc R . .
C4 C 1.0977(5) 1.1188(4) 0.8331(3) 0.0248(7) Uani 1 1 d . . .
H4 H 1.1021 1.2067 0.8022 0.030 Uiso 1 1 calc R . .
C2 C 1.2069(4) 0.9951(4) 0.9570(3) 0.0229(7) Uani 1 1 d . . .
H2 H 1.2889 0.9954 1.0114 0.027 Uiso 1 1 calc R . .
C6 C 1.0419(4) 0.7236(4) 0.9663(2) 0.0177(6) Uani 1 1 d . . .
C11 C 0.3737(4) 0.3395(4) 0.6662(3) 0.0215(7) Uani 1 1 d . . .
H11 H 0.4045 0.2757 0.7103 0.026 Uiso 1 1 calc R . .
C9 C 0.1717(4) 0.3815(4) 0.5439(3) 0.0250(7) Uani 1 1 d . . .
H9 H 0.0651 0.3500 0.5030 0.030 Uiso 1 1 calc R . .
C10 C 0.2174(4) 0.2884(4) 0.6061(3) 0.0241(7) Uani 1 1 d . . .
H10 H 0.1440 0.1909 0.6083 0.029 Uiso 1 1 calc R . .
C3 C 1.2202(5) 1.1229(4) 0.9119(3) 0.0268(8) Uani 1 1 d . . .
H3 H 1.3118 1.2124 0.9345 0.032 Uiso 1 1 calc R . .
H17B H 0.194(5) 0.862(5) 0.618(3) 0.017(11) Uiso 1 1 d . . .
H24B H 0.438(3) 0.803(4) 0.525(2) 0.014(9) Uiso 1 1 d D . .
H16B H 0.505(3) 0.455(5) 0.878(3) 0.019(10) Uiso 1 1 d D . .
H17A H 0.284(7) 0.905(6) 0.695(4) 0.046(14) Uiso 1 1 d . . .
H24A H 0.621(5) 0.898(4) 0.558(4) 0.060(17) Uiso 1 1 d D . .
H13B H 0.590(6) 0.829(3) 0.824(3) 0.040(13) Uiso 1 1 d D . .
H22B H 1.220(4) 0.798(4) 1.077(3) 0.042(13) Uiso 1 1 d D . .
H14B H 1.035(6) 0.678(4) 0.698(4) 0.047(15) Uiso 1 1 d D . .
H22A H 1.105(5) 0.639(4) 1.078(3) 0.032(12) Uiso 1 1 d D . .
H13A H 0.502(4) 0.704(7) 0.850(4) 0.07(2) Uiso 1 1 d D . .
H15B H 0.686(5) 0.267(4) 0.753(4) 0.056(16) Uiso 1 1 d D . .
H14A H 1.059(5) 0.578(6) 0.756(3) 0.050(15) Uiso 1 1 d D . .
H16A H 0.638(7) 0.448(7) 0.941(2) 0.066(18) Uiso 1 1 d D . .
H15A H 0.777(7) 0.289(6) 0.695(3) 0.065(18) 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
Er1 O2 2.263(2) . ?
Er1 O1 2.268(2) . ?
Er1 O3 2.332(2) . ?
Er1 O5 2.337(3) . ?
Er1 O4 2.367(3) . ?
Er1 O6 2.376(2) . ?
Er1 N3 2.498(3) . ?
Er1 N1 2.514(3) . ?
O1 C6 1.253(4) . ?
O2 C12 1.259(4) . ?
N1 C5 1.337(4) . ?
N1 C1 1.360(4) . ?
N3 C11 1.335(4) . ?
N3 C7 1.348(4) . ?
N2 C6 1.306(4) . ?
N4 C12 1.302(4) . ?
C5 C4 1.394(5) . ?
C1 C2 1.379(5) . ?
C1 C6 1.487(5) . ?
C7 C8 1.380(5) . ?
C7 C12 1.510(4) . ?
C8 C9 1.389(5) . ?
C4 C3 1.386(5) . ?
C2 C3 1.377(5) . ?
C11 C10 1.393(5) . ?
C9 C10 1.369(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Er1 O1 143.28(9) . . ?
O2 Er1 O3 79.11(9) . . ?
O1 Er1 O3 99.80(9) . . ?
O2 Er1 O5 117.22(9) . . ?
O1 Er1 O5 86.32(9) . . ?
O3 Er1 O5 142.02(9) . . ?
O2 Er1 O4 80.34(9) . . ?
O1 Er1 O4 81.93(9) . . ?
O3 Er1 O4 147.00(9) . . ?
O5 Er1 O4 70.83(9) . . ?
O2 Er1 O6 139.64(8) . . ?
O1 Er1 O6 71.26(9) . . ?
O3 Er1 O6 72.92(9) . . ?
O5 Er1 O6 73.82(9) . . ?
O4 Er1 O6 136.52(9) . . ?
O2 Er1 N3 66.93(9) . . ?
O1 Er1 N3 149.42(9) . . ?
O3 Er1 N3 78.42(10) . . ?
O5 Er1 N3 77.86(10) . . ?
O4 Er1 N3 116.22(9) . . ?
O6 Er1 N3 79.21(9) . . ?
O2 Er1 N1 77.69(9) . . ?
O1 Er1 N1 66.58(9) . . ?
O3 Er1 N1 76.59(9) . . ?
O5 Er1 N1 138.03(9) . . ?
O4 Er1 N1 73.98(9) . . ?
O6 Er1 N1 121.70(9) . . ?
N3 Er1 N1 139.75(9) . . ?
C6 O1 Er1 125.4(2) . . ?
C12 O2 Er1 122.5(2) . . ?
C5 N1 C1 117.8(3) . . ?
C5 N1 Er1 126.3(2) . . ?
C1 N1 Er1 115.3(2) . . ?
C11 N3 C7 117.6(3) . . ?
C11 N3 Er1 126.9(2) . . ?
C7 N3 Er1 115.0(2) . . ?
N1 C5 C4 122.4(3) . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 C6 113.0(3) . . ?
C2 C1 C6 124.3(3) . . ?
N3 C7 C8 123.2(3) . . ?
N3 C7 C12 112.7(3) . . ?
C8 C7 C12 124.1(3) . . ?
O2 C12 N4 122.1(3) . . ?
O2 C12 C7 118.2(3) . . ?
N4 C12 C7 119.7(3) . . ?
C7 C8 C9 118.1(3) . . ?
C3 C4 C5 119.1(3) . . ?
C3 C2 C1 119.2(3) . . ?
O1 C6 N2 120.7(3) . . ?
O1 C6 C1 118.9(3) . . ?
N2 C6 C1 120.4(3) . . ?
N3 C11 C10 122.8(3) . . ?
C10 C9 C8 119.6(3) . . ?
C9 C10 C11 118.6(3) . . ?
C2 C3 C4 118.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.148


_database_code_depnum_ccdc_archive 'CCDC 918191'
#######################################################################
#
#                 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_sa1756-a
#TrackingRef 'sa1756-a.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H22 N4 Pr O7,3(Br)'
_chemical_formula_sum            'C12 H22 Br3 N4 O7 Pr'
_chemical_formula_weight         714.98

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'
Br Br -0.2901 2.4595 '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   C2/c

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

_cell_length_a                   29.485(6)
_cell_length_b                   7.8780(16)
_cell_length_c                   20.344(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.39(3)
_cell_angle_gamma                90.00
_cell_volume                     4597.1(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7970
_cell_measurement_theta_min      1.4199
_cell_measurement_theta_max      27.4800

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.066
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2736
_exptl_absorpt_coefficient_mu    7.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2319
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11646
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         27.54
_reflns_number_total             5249
_reflns_number_gt                4393
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Mercury: visualization and analysis of crystal structures, C. F. Macrae,
P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELXS-97 (Sheldrick, 1997)'

_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)+(0.0840P)²+23.1609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5249
_refine_ls_number_parameters     244
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1984
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_restrained_S_all      1.231
_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 0.107560(17) 0.22879(7) 0.20939(2) 0.03237(18) Uani 1 1 d D . .
Br1 Br 0.06139(4) 0.71662(14) 0.06702(5) 0.0456(3) Uani 1 1 d . . .
Br2 Br 0.05970(4) 0.74990(14) 0.31954(5) 0.0457(3) Uani 1 1 d . . .
Br3 Br 0.24931(4) 0.45772(17) 0.14416(6) 0.0527(3) Uani 1 1 d . . .
O1 O 0.0652(3) 0.2559(9) 0.0928(3) 0.0443(18) Uani 1 1 d . . .
O2 O 0.0623(2) 0.1942(9) 0.2944(3) 0.0401(16) Uani 1 1 d . . .
O3 O 0.0457(2) 0.0022(9) 0.1782(3) 0.0436(16) Uani 1 1 d . . .
H3A H 0.0493 -0.0563 0.1452 0.052 Uiso 1 1 d R . .
H3B H 0.0332 -0.0312 0.2090 0.052 Uiso 1 1 d R . .
O4 O 0.1970(3) 0.2315(9) 0.2417(4) 0.0488(19) Uani 1 1 d D . .
H4B H 0.2134 0.2021 0.2795 0.059 Uiso 1 1 d RD . .
H4A H 0.2147 0.2587 0.2165 0.059 Uiso 1 1 d RD . .
N3 N 0.1364(3) 0.3925(10) 0.3289(4) 0.0357(17) Uani 1 1 d . . .
N1 N 0.1409(3) 0.0681(11) 0.1117(4) 0.0412(19) Uani 1 1 d . . .
O5 O 0.0494(3) 0.4629(10) 0.1978(3) 0.0501(19) Uani 1 1 d D . .
H5A H 0.0323 0.4955 0.1610 0.060 Uiso 1 1 d RD . .
H5B H 0.0472 0.5312 0.2286 0.060 Uiso 1 1 d RD . .
O7 O 0.1419(3) 0.4846(10) 0.1644(5) 0.066(2) Uani 1 1 d D . .
H7B H 0.1651 0.4800 0.1471 0.079 Uiso 1 1 d RD . .
H7A H 0.1262 0.5711 0.1493 0.079 Uiso 1 1 d RD . .
O6 O 0.1394(3) -0.0295(10) 0.2740(4) 0.057(2) Uani 1 1 d D . .
H6B H 0.1603 -0.0139 0.3094 0.069 Uiso 1 1 d RD . .
H6A H 0.1198 -0.0980 0.2829 0.069 Uiso 1 1 d RD . .
C6 C 0.0789(4) 0.2178(13) 0.0402(4) 0.039(2) Uani 1 1 d . . .
C11 C 0.1726(4) 0.4981(14) 0.3428(6) 0.049(3) Uani 1 1 d . . .
H11 H 0.1878 0.5287 0.3081 0.059 Uiso 1 1 calc R . .
C7 C 0.1146(3) 0.3512(12) 0.3771(5) 0.037(2) Uani 1 1 d . . .
C12 C 0.0721(3) 0.2453(12) 0.3535(5) 0.037(2) Uani 1 1 d . . .
C5 C 0.1781(4) -0.0376(14) 0.1223(5) 0.051(3) Uani 1 1 d . . .
H5 H 0.1915 -0.0742 0.1671 0.061 Uiso 1 1 calc R . .
C1 C 0.1217(4) 0.1145(13) 0.0462(4) 0.038(2) Uani 1 1 d . . .
N2 N 0.0558(4) 0.2661(13) -0.0199(4) 0.057(3) Uani 1 1 d . . .
H2A H 0.0302 0.3264 -0.0242 0.068 Uiso 1 1 calc R . .
H2B H 0.0659 0.2382 -0.0558 0.068 Uiso 1 1 calc R . .
N4 N 0.0452(3) 0.2058(13) 0.3936(4) 0.051(2) Uani 1 1 d . . .
H4C H 0.0202 0.1432 0.3786 0.061 Uiso 1 1 calc R . .
H4D H 0.0519 0.2418 0.4357 0.061 Uiso 1 1 calc R . .
C10 C 0.1885(4) 0.5645(14) 0.4076(6) 0.050(3) Uani 1 1 d . . .
H10 H 0.2135 0.6433 0.4166 0.060 Uiso 1 1 calc R . .
C9 C 0.1680(4) 0.5161(14) 0.4576(5) 0.046(2) Uani 1 1 d . . .
H9 H 0.1801 0.5539 0.5026 0.056 Uiso 1 1 calc R . .
C8 C 0.1298(4) 0.4124(14) 0.4431(5) 0.045(2) Uani 1 1 d . . .
H8 H 0.1139 0.3826 0.4771 0.054 Uiso 1 1 calc R . .
C3 C 0.1787(4) -0.0416(16) 0.0052(6) 0.056(3) Uani 1 1 d . . .
H3 H 0.1919 -0.0771 -0.0309 0.067 Uiso 1 1 calc R . .
C2 C 0.1404(4) 0.0648(15) -0.0063(6) 0.051(3) Uani 1 1 d . . .
H2 H 0.1271 0.1036 -0.0508 0.062 Uiso 1 1 calc R . .
C4 C 0.1972(4) -0.0946(16) 0.0699(6) 0.056(3) Uani 1 1 d . . .
H4 H 0.2231 -0.1701 0.0790 0.067 Uiso 1 1 calc 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 O1 2.421(7) . ?
Pr1 O2 2.432(7) . ?
Pr1 O6 2.486(7) . ?
Pr1 O5 2.492(7) . ?
Pr1 O7 2.520(8) . ?
Pr1 O3 2.525(7) . ?
Pr1 O4 2.566(7) . ?
Pr1 N3 2.709(7) . ?
Pr1 N1 2.725(8) . ?
O1 C6 1.265(12) . ?
O2 C12 1.237(12) . ?
N3 C11 1.332(13) . ?
N3 C7 1.332(12) . ?
N1 C5 1.353(13) . ?
N1 C1 1.370(12) . ?
C6 N2 1.309(13) . ?
C6 C1 1.483(14) . ?
C11 C10 1.394(15) . ?
C7 C8 1.398(14) . ?
C7 C12 1.490(14) . ?
C12 N4 1.302(13) . ?
C5 C4 1.392(15) . ?
C1 C2 1.368(14) . ?
C10 C9 1.352(16) . ?
C9 C8 1.368(15) . ?
C3 C4 1.368(17) . ?
C3 C2 1.381(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Pr1 O2 117.6(2) . . ?
O1 Pr1 O6 129.5(3) . . ?
O2 Pr1 O6 74.6(3) . . ?
O1 Pr1 O5 69.8(2) . . ?
O2 Pr1 O5 70.8(2) . . ?
O6 Pr1 O5 145.4(3) . . ?
O1 Pr1 O7 74.5(3) . . ?
O2 Pr1 O7 132.9(3) . . ?
O6 Pr1 O7 135.4(2) . . ?
O5 Pr1 O7 72.5(3) . . ?
O1 Pr1 O3 68.8(2) . . ?
O2 Pr1 O3 67.4(2) . . ?
O6 Pr1 O3 73.5(2) . . ?
O5 Pr1 O3 93.4(3) . . ?
O7 Pr1 O3 143.3(3) . . ?
O1 Pr1 O4 121.1(3) . . ?
O2 Pr1 O4 121.3(2) . . ?
O6 Pr1 O4 68.4(2) . . ?
O5 Pr1 O4 131.4(2) . . ?
O7 Pr1 O4 67.1(2) . . ?
O3 Pr1 O4 135.2(2) . . ?
O1 Pr1 N3 145.2(2) . . ?
O2 Pr1 N3 61.6(2) . . ?
O6 Pr1 N3 85.0(3) . . ?
O5 Pr1 N3 78.4(2) . . ?
O7 Pr1 N3 82.9(3) . . ?
O3 Pr1 N3 128.3(2) . . ?
O4 Pr1 N3 71.1(2) . . ?
O1 Pr1 N1 61.2(2) . . ?
O2 Pr1 N1 144.8(2) . . ?
O6 Pr1 N1 81.4(3) . . ?
O5 Pr1 N1 129.1(2) . . ?
O7 Pr1 N1 82.1(3) . . ?
O3 Pr1 N1 81.4(2) . . ?
O4 Pr1 N1 70.6(2) . . ?
N3 Pr1 N1 141.7(2) . . ?
C6 O1 Pr1 128.0(7) . . ?
C12 O2 Pr1 127.7(6) . . ?
C11 N3 C7 119.7(8) . . ?
C11 N3 Pr1 123.9(7) . . ?
C7 N3 Pr1 116.1(6) . . ?
C5 N1 C1 117.2(9) . . ?
C5 N1 Pr1 125.8(7) . . ?
C1 N1 Pr1 116.6(6) . . ?
O1 C6 N2 121.5(10) . . ?
O1 C6 C1 119.5(8) . . ?
N2 C6 C1 119.0(9) . . ?
N3 C11 C10 120.8(10) . . ?
N3 C7 C8 121.4(9) . . ?
N3 C7 C12 114.3(8) . . ?
C8 C7 C12 124.2(9) . . ?
O2 C12 N4 119.5(9) . . ?
O2 C12 C7 119.1(9) . . ?
N4 C12 C7 121.4(9) . . ?
N1 C5 C4 122.2(10) . . ?
C2 C1 N1 122.1(10) . . ?
C2 C1 C6 125.6(9) . . ?
N1 C1 C6 112.3(8) . . ?
C9 C10 C11 119.7(10) . . ?
C10 C9 C8 119.6(9) . . ?
C9 C8 C7 118.5(10) . . ?
C4 C3 C2 118.5(11) . . ?
C1 C2 C3 120.2(11) . . ?
C3 C4 C5 119.7(11) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.060
_refine_diff_density_min         -1.048
_refine_diff_density_rms         0.287


_database_code_depnum_ccdc_archive 'CCDC 918192'
